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Chemistry
Organic Building Blocks
Phosphoruses
benzyl
Diethyl 3-Bromobenzylphosphonate
Chemistry
Organic Building Blocks
Synthetic Reagents
Phosphoruses
Benzene Compounds C-C Bond Formation
benzyl
diethyl benzylphosphonate

[ CAS No. 128833-03-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
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Product Details of [ 128833-03-4 ]

CAS No. :128833-03-4 MDL No. :MFCD07772009
Formula : C11H16BrO3P Boiling Point : -
Linear Structure Formula :- InChI Key :KVNNRCDDRDXWIW-UHFFFAOYSA-N
M.W : 307.12 Pubchem ID :10979718
Synonyms :

Safety of [ 128833-03-4 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H302 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 128833-03-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 128833-03-4 ]

[ 128833-03-4 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 54663-78-4 ]
  • [ 128833-03-4 ]
  • (3-Thiophen-2-yl-benzyl)-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% In acetonitrile Heating;
Reference： [1]Kennedy, Gordon; Perboni, Alcide D. [Tetrahedron Letters, 1996, vol. 37, # 42, p. 7611 - 7614]
  • 2
  • [ 17997-47-6 ]
  • [ 128833-03-4 ]
  • Diethyl (3-(pyridin-2-yl)benzyl)phosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
43% In acetonitrile Heating;
Reference： [1]Kennedy, Gordon; Perboni, Alcide D. [Tetrahedron Letters, 1996, vol. 37, # 42, p. 7611 - 7614]
  • 3
  • [ 128833-03-4 ]
  • [ 105494-69-7 ]
  • [3-(1-Methyl-1H-imidazol-2-yl)-benzyl]-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
55% In acetonitrile Heating;
Reference： [1]Kennedy, Gordon; Perboni, Alcide D. [Tetrahedron Letters, 1996, vol. 37, # 42, p. 7611 - 7614]
  • 4
  • [ 128833-03-4 ]
  • [ 144173-85-3 ]
  • (3-Pyrimidin-5-yl-benzyl)-phosphonic acid diethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% In acetonitrile Heating;
Reference： [1]Kennedy, Gordon; Perboni, Alcide D. [Tetrahedron Letters, 1996, vol. 37, # 42, p. 7611 - 7614]
  • 5
  • [ 823-78-9 ]
  • [ 122-52-1 ]
  • [ 128833-03-4 ]
YieldReaction ConditionsOperation in experiment
98% at 130℃; 113 Diethyl[(3-bromophenyl)methyl]phosphonate Example 113 Diethyl[(3-bromophenyl)methyl]phosphonate To 1-bromo-3-(bromomethyl)benzene (100 g, 400 mmol) in a 500 mL round-bottom flask under nitrogen was added triethyl phosphite (69.6 mL, 400 mmol) and the solution was heated to 130° C. The apparatus was set up ready for distillation. As the heating block reached 130° C. the mixture began to reflux and a large volume of colourless liquid was allowed to distill off. Lab HPLC of the reaction after 40 min showed some starting material so another 0.5 eq of the phosphite was added, and heating with distillation continued. The reaction was then heated under vacuum and the excess phosphite was distilled off under vacuum (130° C. heater and 15 mbar, gradually going down to 0.5 mbar). This gave 120.8 g (98%) of a colourless oil that the lab HPLC showed to be 97% pure with a 2.20 min retention time. LC-MS m/z 307, 309 (M+H)+, 1.01 min (ret time).
95.5% at 20 - 150℃; 1 The above bromide (52.7 g, 0.21 mol) was warmed up to 120° C. and then triethyl phosphite (35.0 g, 36.7 mL, 0.21 mol) was added dropwise under stirring. The temperature was increased to 150° C., the mixture was stirred for 6 h and left to stand overnight at room temperature. The residue was distilled to give 61.55 g (95.5%) of (3-bromobenzyl)phosphonic acid diethyl ester, b.p. 124-126° C./13 Pa.
95.5% at 20 - 150℃; 1 The above bromide (52.7 g, 0.21 mol) was warmed up to 120 °C and then triethyl phosphite (35.0 g, 36.7 mL, 0.21 mol) was added dropwise under stirring. The temperature was increased to 150 °C, the mixture was stirred for 6 h and left to stand overnight at room temperature. The residue was distilled to give 61.55 g (95.5 %) of (3-bromobenzyl)- phosphonic acid diethyl ester, b. p. 124-126 °C/13 Pa.
93% at 80℃; for 17h;
91% at 140℃; for 0.0833333h; Microwave irradiation;
90% at 120℃; for 14h;
85% In toluene for 24h; Reflux;
Heating;
for 3h; Heating / reflux;
for 3h; Heating / reflux;
at 130℃; Reflux; Inert atmosphere; 125 Diethyl[(3-bromophenyl)methyl]phosphonate Example 125 Diethyl[(3-bromophenyl)methyl]phosphonate To 1-bromo-3-(bromomethyl)benzene (100 g, 400 mmol) in a 500 mL round-bottom flask under nitrogen was added triethyl phosphite (69.6 mL, 400 mmol) and the solution was heated to 130° C. The apparatus was set up ready for distillation. As the heating block reached 130° C. the mixture began to reflux and a large volume of colourless liquid was allowed to distil off. Analysis of the reaction by hplc after 40 min showed some starting material so another 0.5 eq of the phosphite was added and heating with distillation continued. The reaction was then heated under vacuum: the excess phosphite was distilled off under vacuum (130° C. heater and 15 mbar, gradually going down to 0.5 mbar). This gave a colorless oil 120.8 g. HPLC 2.20 min (ret time), 97%; LC-MS m/z 307, 309 (M+H)+, 1.01 min (ret time).

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2009/203657, 2009, A1 Location in patent: Page/Page column 76-77
[2]Current Patent Assignee: VTV THERAPEUTICS INC. - US2009/12171, 2009, A1 Location in patent: Page/Page column 11
[3]Current Patent Assignee: VTV THERAPEUTICS INC. - WO2005/105736, 2005, A1 Location in patent: Page/Page column 28-29
[4]Location in patent: experimental part Hong, Myeng Chan; Kim, Yun Kyung; Choi, Jae Yong; Yang, Si Qiang; Rhee, Hakjune; Ryu, Young Hoon; Choi, Tae Hyun; Cheon, Gi Jeong; An, Gwang Il; Kim, Hye Yun; Kim, Youngsoo; Kim, Dong Jin; Lee, Jun-Seok; Chang, Young-Tae; Lee, Kyo Chul [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 22, p. 7724 - 7730]
[5]Beletskaya, Irina P.; Titanyuk, Igor D. [Journal of Organic Chemistry, 2022, vol. 87, # 5, p. 2748 - 2757]
[6]Caplan, Neil A.; Pogson, Christopher I.; Hayes, David J.; Blackburn, G. Michael [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 3, p. 421 - 437]
[7]Location in patent: scheme or table Ward, Simon E.; Eddershaw, Peter; Flynn, Sean T.; Gordon, Laurie; Lovell, Peter J.; Moore, Susan H.; Scott, Claire M.; Smith, Paul W.; Thewlis, Kevin M.; Wyman, Paul A. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 428 - 432]
[8]Kennedy, Gordon; Perboni, Alcide D. [Tetrahedron Letters, 1996, vol. 37, # 42, p. 7611 - 7614]
[9]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP1182183, 2002, A1 Location in patent: Page 36
[10]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP1182183, 2002, A1 Location in patent: Page 39
[11]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2009/203677, 2009, A1 Location in patent: Page/Page column 85
  • 6
  • [ 128833-03-4 ]
  • C42H48O6 [ No CAS ]
  • 5,17-bis((E)-2-(3-bromophenyl)-1-ethenyl)-25,26-27,28-tetrapropoxycalix[4]arene [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In tetrahydrofuran at 25℃; for 0.75h;
Reference： [1]Larsen, Mogens; Krebs, Frederik C.; Jorgensen, Mikkel; Harrit, Niels [Journal of Organic Chemistry, 1998, vol. 63, # 13, p. 4420 - 4424]
  • 7
  • Diethyl phosphonate [ No CAS ]
  • [ 128833-03-4 ]
  • [ 263165-27-1 ]
YieldReaction ConditionsOperation in experiment
67% With triethylamine at 100℃; for 22h;
Reference： [1]Caplan, Neil A.; Pogson, Christopher I.; Hayes, David J.; Blackburn, G. Michael [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 3, p. 421 - 437]
  • 8
  • [ 128833-03-4 ]
  • [ 307318-49-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 12 percent / KH / tetrahydrofuran / 4 h / Heating 2: 86 percent / Et3N; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 80 °C 3: 75 percent / tetrahydrofuran / 1.5 h / Irradiation 4: 94 percent / aq. HF / acetonitrile / 3 h / 20 °C 5: 97 percent / PDC / CH2Cl2 / 8 h
Reference： [1]Fernandez-Gacio; Vitale; Mourino [Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 6978 - 6983]
  • 9
  • [ 128833-03-4 ]
  • [ 307318-48-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 12 percent / KH / tetrahydrofuran / 4 h / Heating 2: 86 percent / Et3N; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 80 °C 3: 92 percent / aq. HF / acetonitrile / 3 h / 20 °C 4: 95 percent / PDC / CH2Cl2 / 8 h
Reference： [1]Fernandez-Gacio; Vitale; Mourino [Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 6978 - 6983]
  • 10
  • [ 128833-03-4 ]
  • [ 307318-55-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 12 percent / KH / tetrahydrofuran / 4 h / Heating 2: 86 percent / Et3N; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 80 °C 3: 75 percent / tetrahydrofuran / 1.5 h / Irradiation 4: 94 percent / aq. HF / acetonitrile / 3 h / 20 °C
Reference： [1]Fernandez-Gacio; Vitale; Mourino [Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 6978 - 6983]
  • 11
  • [ 128833-03-4 ]
  • [ 307318-50-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 12 percent / KH / tetrahydrofuran / 4 h / Heating 2: 86 percent / Et3N; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 80 °C 3: 92 percent / aq. HF / acetonitrile / 3 h / 20 °C
Reference： [1]Fernandez-Gacio; Vitale; Mourino [Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 6978 - 6983]
  • 12
  • [ 128833-03-4 ]
  • [ 307318-54-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 12 percent / KH / tetrahydrofuran / 4 h / Heating 2: 86 percent / Et3N; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 80 °C 3: 75 percent / tetrahydrofuran / 1.5 h / Irradiation
Reference： [1]Fernandez-Gacio; Vitale; Mourino [Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 6978 - 6983]
  • 13
  • [ 128833-03-4 ]
  • [ 282724-94-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 12 percent / KH / tetrahydrofuran / 4 h / Heating 2: 86 percent / Et3N; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 80 °C
Reference： [1]Fernandez-Gacio; Vitale; Mourino [Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 6978 - 6983]
  • 14
  • [ 128833-03-4 ]
  • (17Z)-1α-20-[3-(dimethylhydroxymethyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 8 steps 1: 12 percent / KH / tetrahydrofuran / 4 h / Heating 2: 86 percent / Et3N; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 80 °C 3: 75 percent / tetrahydrofuran / 1.5 h / Irradiation 4: 94 percent / aq. HF / acetonitrile / 3 h / 20 °C 5: 97 percent / PDC / CH2Cl2 / 8 h 6: 94 percent / n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 7: 98 percent / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C 8: 85 percent / TBAF / tetrahydrofuran / 26 h / 20 °C
Reference： [1]Fernandez-Gacio; Vitale; Mourino [Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 6978 - 6983]
  • 15
  • [ 128833-03-4 ]
  • (17E)-1α-20-[3-(dimethylhydroxymethyl)phenyl]-17,20-didehydro-21,22,23,24,25,26,27-heptanorvitamin D3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 12 percent / KH / tetrahydrofuran / 4 h / Heating 2: 86 percent / Et3N; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 80 °C 3: 92 percent / aq. HF / acetonitrile / 3 h / 20 °C 4: 95 percent / PDC / CH2Cl2 / 8 h 5: 94 percent / n-BuLi / tetrahydrofuran; hexane / 6 h / -78 - -40 °C 6: 90 percent / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C 7: 90 percent / TBAF / tetrahydrofuran / 26 h / 20 °C
Reference： [1]Fernandez-Gacio; Vitale; Mourino [Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 6978 - 6983]
  • 16
  • [ 128833-03-4 ]
  • [ 307318-56-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 12 percent / KH / tetrahydrofuran / 4 h / Heating 2: 86 percent / Et3N; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 80 °C 3: 75 percent / tetrahydrofuran / 1.5 h / Irradiation 4: 94 percent / aq. HF / acetonitrile / 3 h / 20 °C 5: 97 percent / PDC / CH2Cl2 / 8 h 6: 94 percent / n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C
Reference： [1]Fernandez-Gacio; Vitale; Mourino [Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 6978 - 6983]
  • 17
  • [ 128833-03-4 ]
  • [ 307318-51-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 12 percent / KH / tetrahydrofuran / 4 h / Heating 2: 86 percent / Et3N; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 80 °C 3: 92 percent / aq. HF / acetonitrile / 3 h / 20 °C 4: 95 percent / PDC / CH2Cl2 / 8 h 5: 94 percent / n-BuLi / tetrahydrofuran; hexane / 6 h / -78 - -40 °C
Reference： [1]Fernandez-Gacio; Vitale; Mourino [Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 6978 - 6983]
  • 18
  • [ 128833-03-4 ]
  • [ 307318-57-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 12 percent / KH / tetrahydrofuran / 4 h / Heating 2: 86 percent / Et3N; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 80 °C 3: 75 percent / tetrahydrofuran / 1.5 h / Irradiation 4: 94 percent / aq. HF / acetonitrile / 3 h / 20 °C 5: 97 percent / PDC / CH2Cl2 / 8 h 6: 94 percent / n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C 7: 98 percent / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C
Reference： [1]Fernandez-Gacio; Vitale; Mourino [Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 6978 - 6983]
  • 19
  • [ 128833-03-4 ]
  • [ 307318-52-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 12 percent / KH / tetrahydrofuran / 4 h / Heating 2: 86 percent / Et3N; dppp / Pd(OAc)2 / dimethylsulfoxide / 12 h / 80 °C 3: 92 percent / aq. HF / acetonitrile / 3 h / 20 °C 4: 95 percent / PDC / CH2Cl2 / 8 h 5: 94 percent / n-BuLi / tetrahydrofuran; hexane / 6 h / -78 - -40 °C 6: 90 percent / tetrahydrofuran; diethyl ether / 0.75 h / -78 °C
Reference： [1]Fernandez-Gacio; Vitale; Mourino [Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 6978 - 6983]
  • 20
  • [ 128833-03-4 ]
  • (3-Phosphonophenyl)methylphosphonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 67 percent / NEt3 / Pd(PPh3)4 / 22 h / 100 °C 2: CH2Cl2 / 22 h / 20 °C 3: MeOH / CH2Cl2
Reference： [1]Caplan, Neil A.; Pogson, Christopher I.; Hayes, David J.; Blackburn, G. Michael [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 3, p. 421 - 437]
  • 21
  • [ 128833-03-4 ]
  • (3-Phosphonophenyl)difluoromethylphosphonic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: 67 percent / NEt3 / Pd(PPh3)4 / 22 h / 100 °C 2.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C 2.2: 53 percent / N-fluorobisbenzenesulfonimide / tetrahydrofuran / 2 h / -78 °C 3.1: CH2Cl2 / 22 h / 20 °C 4.1: MeOH / CH2Cl2
Reference： [1]Caplan, Neil A.; Pogson, Christopher I.; Hayes, David J.; Blackburn, G. Michael [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 3, p. 421 - 437]
  • 22
  • [ 128833-03-4 ]
  • [ 263164-70-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: 67 percent / NEt3 / Pd(PPh3)4 / 22 h / 100 °C 2.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C 2.2: 53 percent / N-fluorobisbenzenesulfonimide / tetrahydrofuran / 2 h / -78 °C
Reference： [1]Caplan, Neil A.; Pogson, Christopher I.; Hayes, David J.; Blackburn, G. Michael [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 3, p. 421 - 437]
  • 23
  • [ 128833-03-4 ]
  • C19H42O6P2Si4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 67 percent / NEt3 / Pd(PPh3)4 / 22 h / 100 °C 2: CH2Cl2 / 22 h / 20 °C
Reference： [1]Caplan, Neil A.; Pogson, Christopher I.; Hayes, David J.; Blackburn, G. Michael [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 3, p. 421 - 437]
  • 24
  • [ 128833-03-4 ]
  • C19H40F2O6P2Si4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: 67 percent / NEt3 / Pd(PPh3)4 / 22 h / 100 °C 2.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C 2.2: 53 percent / N-fluorobisbenzenesulfonimide / tetrahydrofuran / 2 h / -78 °C 3.1: CH2Cl2 / 22 h / 20 °C
Reference： [1]Caplan, Neil A.; Pogson, Christopher I.; Hayes, David J.; Blackburn, G. Michael [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2000, # 3, p. 421 - 437]
  • 25
  • [ 100-52-7 ]
  • [ 128833-03-4 ]
  • [ 14064-45-0 ]
YieldReaction ConditionsOperation in experiment
77% With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 0 - 20℃;
Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP1182183, 2002, A1 Location in patent: Page 36
  • 26
  • [ 128833-03-4 ]
  • [ 98-86-2 ]
  • 3-bromo-β-methystilbene [ No CAS ]
YieldReaction ConditionsOperation in experiment
63% With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 0 - 20℃;
Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP1182183, 2002, A1 Location in patent: Page 39
  • 27
  • [ 268232-19-5 ]
  • [ 128833-03-4 ]
  • [ 268232-20-8 ]
YieldReaction ConditionsOperation in experiment
89% With 15-crown-5; sodium hydride In tetrahydrofuran at 20℃; 1.g g) 3-Bromo-[2-(3-ethoxymethoxy-5-ethoxymethoxymethylphenyl)vinyl]phenyl. 290 mg (8.9 mmol) of sodium hydride 75% are added, in small quantities, to a solution of 2 g [00255] (7.4 mmol) of 3-ethoxymethoxy-5-ethoxymethoxymethylbenzaldehyde and 2.7 g (8.8 mmol) of ethyl (3-bromobenzyl)phosphonate in 60 ml of THF with one drop of 15-Crown-5. The mixture is stirred overnight at room temperature. It is then concentrated, taken up in ethyl ether and washed several times with water. After decantation, the organic phase is dried over magnesium sulphate and concentrated. The residue is purified on a silica column (ethyl acetate 10-heptane 90). [00256] Yellow oil. m=2.8 g. Y=89%. 1H NMR (CDCl3): 1.18-1.28 (6H, m), 3.63-3.79 (4H, m), 4.60 (2H, s), 4.79 (2H, s), 5.26 (2H, s), 6.96 (1H, s), 7.03-7.04 (2H, d), 7.11-7.16 (1H, d, J=12.1 Hz), 7.22-7.25 (1H, d, J=7.8 Hz), 7.36-7.42 (2H, m), 7.65-7.66 (1H, t).
Reference： [1]Current Patent Assignee: Eqt Partners AB; Galderma (in: EQT Partners) - US6689922, 2004, B1 Location in patent: Page column 13
  • 28
  • [ 128833-03-4 ]
  • [ 119-67-5 ]
  • [ 869070-21-3 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: P-[(3-bromophenyl)methyl]phosphonic acid diethyl ester; o-carboxybenzaldehyde With sodium methylate In methanol; N,N-dimethyl-formamide at 5 - 20℃; for 0.666667h; Stage #2: With hydrogenchloride In methanol; water; N,N-dimethyl-formamide at 5℃; 1 Sodium (6.9 g (0.3 mol) was melted in argon atmosphere on oil bath (130° C.). Methanol (10.1 g, 12.75 mL, 0.315 mol) was added dropwise under slow stirring with mechanical stirrer at 140-150° C. during 30 min. Pulverous sodium methoxide was heated at 140° C. for next 30 min, cooled down to 20° C. and dimethylformamide (30 mL) was added. The mixture was cooled to 5° C. and then a solution of above phosphonic ester (36.9 g, 0.12 mol) and phtalaldehydic acid (18.0 g, 0.12 mol) in dimethylformamide (30 mL) was added dropwise under cooling during 10 min (temperature was maintained between 10-20° C.). The reaction mixture was stirred for next 30 min at room temperature, cooled to 5° C., the mixture of conc. hydrochloric acid (20 mL) and water (150 mL) were added dropwise and the product was extracted with chloroform (100 mL, 2×30 mL). The combined organic solution were washed with water (2×80 mL) and evaporated in vacuo. The residue was stirred with water (350 mL) for 2 h, solid was filtered, washed with water (500 mL) and dried. This afforded 32.6 g (90%) of crude 2-[2-(3-bromo-phenyl)-vinyl]-benzoic acid, m.p. 145-150° C. RF 0.75 (SiO2, ethyl acetate/ethanol/acetic acid 60:40:1).
90% Stage #1: P-[(3-bromophenyl)methyl]phosphonic acid diethyl ester; o-carboxybenzaldehyde With methanol; sodium In DMF (N,N-dimethyl-formamide) at 5 - 150℃; for 1.5h; Stage #2: With hydrogenchloride; water In DMF (N,N-dimethyl-formamide) at 5℃; 1 Sodium (6.9 g (0.3 mol) was melted in argon atmosphere on oil bath (130 °C). Methanol (10.1 g, 12.75 mL, 0.315 mol) was added dropwise under slow stirring with me- chanical stirrer at 140-150 °C during 30 min. Pulverous sodium methoxide was heated at 140 °C for next 30 min, cooled down to 20 °C and dimethylformamide (30 mL) was added. The mixture was cooled to 5 °C and then a solution of above phosphonic ester (36.9 g, 0.12 mol) and phtalaldehydic acid (18.0 g, 0.12 mol) in dimethylformamide (30 mL) was added drop- wise under cooling during 10 min (temperature was maintained between 10-20 °C). The re- action mixture was stirred for next 30 min at room temperature, cooled to 5 °C, the mixture of conc. hydrochloric acid (20 mL) and water (150 mL) were added dropwise and the product was extracted with chloroform (100 mL, 2 x 30 mL). The combined organic solution were washed with water (2 x 80 mL) and evaporated in vacuo. The residue was stirred with water (350 mL) for 2 h, solid was filtered, washed with water (500 mL) and dried. This afforded 32.6 g (90 %) of crude 2- [2-(3-bromo-phenyl)-vinyl]-benzoic m. p. 145-150 °C. RF 0.75 (Si02, ethyl acetate/ethanol/acetic acid 60:40:1).
Reference： [1]Current Patent Assignee: VTV THERAPEUTICS INC. - US2009/12171, 2009, A1 Location in patent: Page/Page column 11-12
[2]Current Patent Assignee: VTV THERAPEUTICS INC. - WO2005/105736, 2005, A1 Location in patent: Page/Page column 29
  • 29
  • [ 823-78-9 ]
  • [ 128833-03-4 ]
YieldReaction ConditionsOperation in experiment
44.02 g (72%) With triethyl phosphite 2 Preparation of diethyl 3-bromobenzylphosphonate (B) EXAMPLE 2 Preparation of diethyl 3-bromobenzylphosphonate (B) 50 g (0.2 mol) of 3-bromobenzyl bromide and 33.2 g (0.2 mol) of triethyl phosphite were heated at 140° C. for 2 hours, during which ethyl bromide was distilled off. The product was distilled over a 30 cm Vigreux column. Yield: 44.02 g (72%); boiling point: 140°-148° C./0.7-0.8 mm; 1 H-NMR (60 MHz, CDCl3 /TMS): δ=1.21 (t,6H,P--O--CH2 --CH3), 3.10 (d,2H,CH2 --P) JPH =22 Hz, 4.03 (dq,4H,P--O--CH2 --CH3), 7.04-7.61 (m,4H,Ar--H).
Reference： [1]Current Patent Assignee: HOECHSST - US5242908, 1993, A
  • 30
  • [ 532-24-1 ]
  • [ 128833-03-4 ]
  • [ 1177559-70-4 ]
YieldReaction ConditionsOperation in experiment
85% With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 5h; 183 Example 183 3-[(3-Bromophenyl)methylidene]-8-methyl-8-azabicyclo[3.2.1]octane To a solution of diethyl [(3-bromophenyl)methyl]phosphonate (3.07 g, 10 mmol) in THF (20 mL) was added 8-methyl-8-azabicyclo[3.2.1]octan-3-one (1.67 g, 12 mmol) then KOBu-t (1.234 g, 11 mmol). The reaction mixture was stirred at room temperature for 5 h before it was quenched with NH4Cl (5 mL, saturated aqueous). The organic layer of the reaction mixture was separated and the aqueous layer was extracted with DCM (5 mL). The combined organic layers were loaded onto a Combiflash Redisep silica gel column (40 g) and purified by Combiflash chromatograph to afford 2.48 g (85%) of the title compound. LC-MS m/z 292 (M+H)+.
Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2009/197871, 2009, A1 Location in patent: Page/Page column 108
  • 31
  • [ 79099-07-3 ]
  • [ 128833-03-4 ]
  • [ 163210-03-5 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydride In tetrahydrofuran at 20℃; for 4h;
83% With potassium <i>tert</i>-butylate In tetrahydrofuran at 20 - 25℃; Inert atmosphere; 126 1,1-Dimethylethyl 4-[(3-bromophenyl)methylidene]-1-piperidinecarboxylate Example 126 1,1-Dimethylethyl 4-[(3-bromophenyl)methylidene]-1-piperidinecarboxylate To diethyl[(3-bromophenyl)methyl]phosphonate (100 g, 326 mmol) in a 2 L 3-neck flask with mechanical stirrer was added tetrahydrofuran (THF) (700 mL) followed by 1,1-dimethylethyl 4-oxo-1-piperidinecarboxylate (71.4 g, 358 mmol) and potassium tert-butoxide (38.4 g, 342 mmol), portion-wise with ice-bath cooling to keep the temperature between 20° C. and 25° C. The mixture became more orange and was then stirred at room temperature under nitrogen. Some material was present as a suspension and it was slightly more viscous. Another 3.8 g (0.1 eq) of potassium tert-butoxide was added. After 1.25 h the mixture had practically gelled: an extra 150 mL of THF were added. The mixture was partitioned between water and ethyl acetate and the aqueous layer extracted well with ethyl acetate. The combined organics were washed with water, brine, dried (MgSO4), filtered and evaporated to give a pale yellow oil, 120.73 g. The crude product was purified on a 750 g Companion XL silica cartridge, eluding with 0-25% ethyl acetate in cyclohexane over 8 column volumes. This gave a colorless oil which became a white solid, 94.68 g (83%). HPLC 2.97 min (ret time), 99.5%; LC-MS m/z 352,354 (M+H)+, 3.96 min (ret time).
Reference： [1]Location in patent: scheme or table Ward, Simon E.; Eddershaw, Peter; Flynn, Sean T.; Gordon, Laurie; Lovell, Peter J.; Moore, Susan H.; Scott, Claire M.; Smith, Paul W.; Thewlis, Kevin M.; Wyman, Paul A. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 428 - 432]
[2]Current Patent Assignee: GLAXOSMITHKLINE PLC - US2009/203677, 2009, A1 Location in patent: Page/Page column 85
  • 32
  • [ 878-00-2 ]
  • [ 128833-03-4 ]
  • [ 18951-48-9 ]
YieldReaction ConditionsOperation in experiment
68% With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;
Reference： [1]Location in patent: experimental part Kimura, Mutsumi; Miki, Noritoshi; Adachi, Naoya; Tatewaki, Yoko; Ohta, Kazuchika; Shirai, Hirofusa [Journal of Materials Chemistry, 2009, vol. 19, # 8, p. 1086 - 1092]
  • 33
  • [ 1201-91-8 ]
  • [ 128833-03-4 ]
  • [ 1258962-89-8 ]
YieldReaction ConditionsOperation in experiment
36% With sodium hydride In tetrahydrofuran; mineral oil for 5h; Reflux;
Reference： [1]Location in patent: experimental part Hong, Myeng Chan; Kim, Yun Kyung; Choi, Jae Yong; Yang, Si Qiang; Rhee, Hakjune; Ryu, Young Hoon; Choi, Tae Hyun; Cheon, Gi Jeong; An, Gwang Il; Kim, Hye Yun; Kim, Youngsoo; Kim, Dong Jin; Lee, Jun-Seok; Chang, Young-Tae; Lee, Kyo Chul [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 22, p. 7724 - 7730]
  • 34
  • [ 94-21-3 ]
  • [ 128833-03-4 ]
  • [ 1258962-90-1 ]
YieldReaction ConditionsOperation in experiment
43% With sodium hydride In tetrahydrofuran; mineral oil for 5h; Reflux;
Reference： [1]Location in patent: experimental part Hong, Myeng Chan; Kim, Yun Kyung; Choi, Jae Yong; Yang, Si Qiang; Rhee, Hakjune; Ryu, Young Hoon; Choi, Tae Hyun; Cheon, Gi Jeong; An, Gwang Il; Kim, Hye Yun; Kim, Youngsoo; Kim, Dong Jin; Lee, Jun-Seok; Chang, Young-Tae; Lee, Kyo Chul [Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 22, p. 7724 - 7730]
  • 35
  • [ 15852-73-0 ]
  • [ 122-52-1 ]
  • [ 128833-03-4 ]
YieldReaction ConditionsOperation in experiment
71% With zinc(II) iodide In toluene for 12h; Inert atmosphere; Reflux;
71% With zinc(II) iodide In toluene at 140℃;
Reference： [1]Barney, Rocky J.; Richardson, Rebekah M.; Wiemer, David F. [Journal of Organic Chemistry, 2011, vol. 76, # 8, p. 2875 - 2879]
[2]Richardson, Rebekah M.; Wiemer, David F. [Organic Syntheses, 2013, vol. 90, p. 145 - 152]
  • 36
  • [ 500-22-1 ]
  • [ 128833-03-4 ]
  • [ 128587-88-2 ]
YieldReaction ConditionsOperation in experiment
With sodium methylate In N,N-dimethyl-formamide at 120℃; for 2h; Intermediate 34(E)-3-(3-Bromostyryl)pyridine. To diethyl 3-bromobenzylphosphonate(Kennedy, G. Perboni, A. D. Tetrahedron Lett. 1996, 37, 7611-7614; 1.91 g, 6.22 mmol) in dimethylformamide (20 mL) was added sodium methanolate (0.672 g, 12.44 mmol) followed by 18-crown-6 (0.658 g, 2.488 mmol) and nicotinaldehyde (0.666 g, 6.22 mmol). The reaction mixture was heated to 120°C for 2h at which time the heating bath was turned off and the reaction mixture was allowed to reach ambient temperature over 18 h. The mixture was poured into water and extracted with 3x75 mL ethyl acetate. The combined organics were washed with brine, dried over MgSC , filtered and concentrated in vacuo to 1.7 g amber liquid which was loaded onto a 90 g silica gel cartridge and eluted with 5 to 60% ethyl acetate / hexanes over 1300 mL. The major spot (Rf=0.45; 50% ethyl acetate / hexanes; UV) was collected and concentrated to 939 mg as a colorless oil. XH NMR (500 MHz, CHLOROFORM-d) δ ppm 8.72 (1 H, d, J=1.83 Hz), 8.50 (1 H, dd, J=4.73, 1.68 Hz), 7.81 (1 H, dt, J=8.01, 1.95 Hz), 7.67 (1 H, t, J=1.68 Hz), 7.37 - 7.46 (2 H, m), 7.29 (1 H, dd, J=7.93, 4.88 Hz), 7.20 - 7.25 (1 H, m), 7.07 (2 H, s).
Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - WO2012/64603, 2012, A1 Location in patent: Page/Page column 66-67
  • 37
  • [ 5765-65-1 ]
  • [ 128833-03-4 ]
  • [ 1582788-28-0 ]
YieldReaction ConditionsOperation in experiment
94% Stage #1: P-[(3-bromophenyl)methyl]phosphonic acid diethyl ester With bis(2,2,6,6-tetramethyl-1-piperidyl)zinc In toluene at 20℃; for 1h; Stage #2: 4-(benzoyloxy)morpholine With [2,2]bipyridinyl; copper dichloride In tetrahydrofuran; toluene at 20℃;
Reference： [1]McDonald, Stacey L.; Wang, Qiu [Angewandte Chemie - International Edition, 2014, vol. 53, # 7, p. 1867 - 1871][Angew. Chem., 2014, vol. 126, # 7, p. 1898 - 1902,5]
  • 38
  • [ 5257-24-9 ]
  • [ 128833-03-4 ]
  • (E)-2-(3-bromostyryl)-3-methyl-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With sodium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 1.25h;
Reference： [1]Bera, Kalisankar; Schneider, Christoph [Chemistry - A European Journal, 2016, vol. 22, # 21, p. 7074 - 7078]
  • 39
  • [ 1122-91-4 ]
  • [ 128833-03-4 ]
  • [ 23958-26-1 ]
YieldReaction ConditionsOperation in experiment
94% With potassium <i>tert</i>-butylate In tetrahydrofuran for 0.666667h;
Reference： [1]Gök, Yaşar; Kiliçarslan, Seda; Gök, Halil Zeki; Karayiğit, İlker Ümit [Chirality, 2016, p. 593 - 598]
  • 40
  • [ 3132-99-8 ]
  • [ 128833-03-4 ]
  • [ 23958-26-1 ]
YieldReaction ConditionsOperation in experiment
92% With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.666667h; Inert atmosphere;
Reference： [1]Gök, Yaşar; Kiliçarslan, Seda; Gök, Halil Zeki; Karayiğit, İlker Ümit [Chirality, 2016, p. 593 - 598]
  • 41
  • [ 128833-03-4 ]
  • [ 98977-36-7 ]
  • tert-butyl 3-(3-bromobenzylidene)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium t-butanolate In tetrahydrofuran at -20 - 20℃; Inert atmosphere; 163.1 Step 1:
(E+Z)-tert-butyl 3-(3-bromobenzylidene)piperidine-1-carboxylate To P-[(3-bromophenyl)methyl]-, diethyl ester-phosphonic acid, (0.681 g, 2.22 mmol) in anhydrous THF was added N-Boc-3-piperidone (0.372 g, 1.85 mmol). The mixture was placed into an ice bath salt slurry (-20° C.) for 15 min. under argon. Once sufficiently cool sodium tert-butoxide (0.222 g, 2.22 mmol) was added in batches. The reaction was allowed to warm to rt and stir overnight. The reaction appeared to be complete, as determined by HPLC and AcOH (4 mL) was added to quench. The mixture was then diluted into 100 mL EtOAc and extracted with NaHCO3 (2*100 mL), treated with brine (50 mL). The organic partitions were dried over Na2SO4 and then concentrated to an oil. The title compound was then isolated by flash chromatography using silica gel (EtOAc/Hex). ESI-MS (m/z): 353 [M+1]+.
Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH - US9586928, 2017, B2 Location in patent: Page/Page column 166
  • 42
  • [ 128833-03-4 ]
  • [ 23958-26-1 ]
YieldReaction ConditionsOperation in experiment
90% Stage #1: P-[(3-bromophenyl)methyl]phosphonic acid diethyl ester With sodium t-butanolate In N,N-dimethyl-formamide at 25℃; for 0.0833333h; Inert atmosphere; Stage #2: With oxygen In N,N-dimethyl-formamide at 25℃; for 8h; stereoselective reaction;
Reference： [1]Huang, Tianzeng; Chen, Tieqiao; Han, Li-Biao [Journal of Organic Chemistry, 2018, vol. 83, # 5, p. 2959 - 2965]
  • 43
  • [ 823-78-9 ]
  • [ 762-04-9 ]
  • [ 128833-03-4 ]
YieldReaction ConditionsOperation in experiment
95% Stage #1: phosphonic acid diethyl ester With sodium hydride In N,N-dimethyl-formamide for 0.5h; Cooling with ice; Inert atmosphere; Stage #2: meta-bromobenzyl bromide In N,N-dimethyl-formamide at 20℃; for 8.5h; Inert atmosphere;
Reference： [1]Huang, Tianzeng; Chen, Tieqiao; Han, Li-Biao [Journal of Organic Chemistry, 2018, vol. 83, # 5, p. 2959 - 2965]
  • 44
  • [ 128833-03-4 ]
  • [ 869070-31-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: methanol; sodium / DMF (N,N-dimethyl-formamide) / 1.5 h / 5 - 150 °C 1.2: 5 °C 2.1: ammonia / water / 0.5 h / 50 °C / Charcoal 2.2: 0.5 h / 47 °C / 15201 - 22801.5 Torr 2.3: pH 2 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C 4.1: sodium carbonate / tetrakis(triphenylphosphine) palladium(0) / ethanol; water; toluene / 2.5 h / Heating / reflux
Multi-step reaction with 4 steps 1.1: methanol; sodium / DMF (N,N-dimethyl-formamide) / 1.5 h / 5 - 150 °C 1.2: 5 °C 2.1: ammonia / water / 0.5 h / 50 °C / Charcoal 2.2: 0.5 h / 47 °C / 15201 - 22801.5 Torr 2.3: pH 2 3.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 1 h / 20 °C 4.1: iodine; magnesium; ethylene dibromide / tetrahydrofuran / 1 h / 65 °C / Heating / reflux 4.2: 3.5 h / 35 °C
Reference： [1]Current Patent Assignee: VTV THERAPEUTICS INC. - WO2005/105736, 2005, A1
[2]Current Patent Assignee: VTV THERAPEUTICS INC. - WO2005/105736, 2005, A1
  • 45
  • [ 78-40-0 ]
  • [ 823-78-9 ]
  • [ 128833-03-4 ]
YieldReaction ConditionsOperation in experiment
100% at 160℃; for 2h; 1.1-1; 2.2-1; 22.22-1; 29.29-1; 32.32-1 1-1) Preparation of diethyl 3-bromobenzylphosphonate 10.00 g of 1-bromo-3 (bromomethyl) benzene and 9.97 g of triethylphosphate were stirred at 160 ° C. for 2 hours.At the end of the reaction, the solution was concentrated under reduced pressure at 75 ° C to remove bromoethane and excess triethyl phosphate.Diethyl 3-bromobenzylphosphonate was obtained. (11.65 g, yield 100.0%).
Reference： [1]Current Patent Assignee: SAMYANG HOLDINGS CORPORATION - KR102006994, 2019, B1 Location in patent: Page/Page column 21; 22; 31; 35; 37
  • 46
  • [ 128833-03-4 ]
  • [ 6630-33-7 ]
  • 1-(2-bromophenyl)-2-(3-bromophenyl)ethene [ No CAS ]
YieldReaction ConditionsOperation in experiment
75.3% Stage #1: P-[(3-bromophenyl)methyl]phosphonic acid diethyl ester With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: ortho-bromobenzaldehyde In tetrahydrofuran at 0 - 20℃; for 12h; 1.1-2 1-2) Preparation of 2,3'-(ethene-1,2-diyl)bis(bromobenzene) 0.91 g of sodium hydride and tetrahydrofuran in the reactor100 mL was added.After cooling to 0oC, diethyl 3-bromobenzylphosphonate 10.0g was slowly added.After warming to room temperature, the mixture was stirred for 1 hour.After cooling to 0oC, 6.36 g of 2-bromobenzaldehyde diluted in 50 mL of tetrahydrofuran was slowly added dropwise, and then heated to room temperature, followed by stirring for 12 hours.100 mL of ice water was added, the reaction was completed, and 200 mL of diethyl ether was added and extracted.The organic layer was washed with brine, and 5 g of anhydrous magnesium sulfate was added thereto, followed by stirring for 30 minutes.The organic layer was filtered and concentrated under reduced pressure. The concentrated residue was subjected to silica gel chromatography (hexane / dichloromethane = 3/1) to give 2,3 '-(ethene-1,2-diyl) bis (bromobenzene). (8.74g, yield 75.3%)
Reference： [1]Current Patent Assignee: SAMYANG HOLDINGS CORPORATION - KR102006994, 2019, B1 Location in patent: Paragraph 0193; 0197-0199
  • 47
  • [ 17119-73-2 ]
  • [ 128833-03-4 ]
  • diethyl 2-(3-bromophenyl)-2-[6-chloro-2-(methylthio)pyrimidin-4-yl]methylphosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With sodium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 2h; Inert atmosphere; General Procedure 1 (GP-1) with NaHMDS General procedure: In a 2-dram septum capped reaction vial equipped with a stir barand argon balloon was added phosphonates of a general structure 24 (0.275 mmol, 1.1 eq.) and pyrimidine 24(0.250 mmol, 1 eq.) along with THF (2.5 mL, 0.1 M). The solution was cooled to -78 C and NaHMDS (0.275 mL,0.550 mmol, 2.2 eq., 2 M in THF) was added. The reactions were monitored at -78 C and warmed to roomtemperature when needed (see reaction times below). Once full consumption or no further consumption wasobserved (monitored by TLC and LC/MS), the reactions were quenched with saturated aqueous NH4Cl (8 mL)and water (5 mL). The aqueous layer was extracted with EtOAc or DCM (15 mL x 4), dried over Na2SO4, filteredand concentrated. Further purification by silica gel column chromatography using hexanes/EtOAc orDCM/MeOH provided the desired products.
Reference： [1]Shultz, Zachary; Shan, Chuan; Wojtas, Lukasz; Lopchuk, Justin M. [Arkivoc, 2020, vol. 2021, # 5, p. 73 - 96]
  • 48
  • [(3-bromophenyl)methyl]phosphonic acid [ No CAS ]
  • [ 78-39-7 ]
  • [ 128833-03-4 ]
YieldReaction ConditionsOperation in experiment
74% at 90℃; for 24h; Green chemistry; 3.6. General Procedure for Esterification of Phosphonic Acids 1 Using Triethyl Orthoacetate Leading to Diethyl Phosphonic Esters 4 General procedure: Phosphonic acid 1 (1 mmol) and triethyl orthoacetate (5.5 mL, 30 mmol) were stirred at 90 °C (or, for sparingly soluble substrates, at a higher temperature) for 24 h under a reflux condenser. The progress of the reaction was monitored by31P NMR. The excess of orthoester was evaporated under reduced pressure and the product-dialkyl phosphonate 4-was received in pure form. In some cases, the purity of diester4was not satisfactory and additional purification by bulb-to-bulb vacuum distillation with Kugelrohr apparatus or column chromatography was performed.
Reference： [1]Trzepizur, Damian; Brodzka, Anna; Koszelewski, Dominik; Ostaszewski, Ryszard [Molecules, 2021, vol. 26, # 18]
  • 49
  • [ 128833-03-4 ]
  • [ 73183-34-3 ]
  • diethyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylphosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
60.9% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 90℃; for 4h; 2 To a stirred solution of compound 356-1 (1.0 mg, 3.25 mmol) in dioxane (15 mL) was mg, 6.4 mmol), Pd(dppf)Ch (114 mg, 0.156 mmol). The resulting reaction mixture was heated to 90 °C and stirred for 4 h and concentrated in vacuo to remove the solvent, then added water, the aqueous phase was extracted with dichlorom ethane, the combined organic phases were dried over anhydrous sodium sulfate, filtered, and concentrated, the crude was purified by reverse C.C. to give 356-2 (700 mg, yield: 60.9%) as a yellow solid.
Reference： [1]Current Patent Assignee: UNIVERSITY OF CALIFORNIA; SHANGPHARMA INNOVATION INC - WO2021/155004, 2021, A1 Location in patent: Paragraph 1358-1360
  • 50
  • [ 128833-03-4 ]
  • diethyl 1-(3-bromophenyl)-1-diazomethylphosphonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
16% With 4-toluenesulfonyl azide; potassium-t-butoxide In benzene at 20℃; for 1h; Inert atmosphere;
Reference： [1]Beletskaya, Irina P.; Titanyuk, Igor D. [Journal of Organic Chemistry, 2022, vol. 87, # 5, p. 2748 - 2757]

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