[ CAS No. 517920-60-4 ] 2-(2-Fluorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Cat. No.: A418761

2D 3D

Structure of 517920-60-4 * Storage: Sealed in dry,Store in freezer, under -20°C

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Quality Control of [ 517920-60-4 ]

COA NMR CNMR HPLC LC-MS

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Specification

Alternatived Products of [ 517920-60-4 ]

Product Details of [ 517920-60-4 ]

CAS No. :	517920-60-4	MDL No. :	MFCD10698520
Formula :	C₁₃H₁₈BFO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ABOCFFXSSUAFRP-UHFFFAOYSA-N
M.W :	236.09	Pubchem ID :	53216796
Synonyms :

Safety of [ 517920-60-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 517920-60-4 ]

* 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.

Upstream synthesis route of [ 517920-60-4 ]
Downstream synthetic route of [ 517920-60-4 ]

[ 517920-60-4 ] Synthesis Path-Upstream 1~4

1
[ 345-35-7 ]
[ 73183-34-3 ]
[ 517920-60-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With iron(III)-acetylacetonate; magnesium In tetrahydrofuran at 0℃; for 3 h; Inert atmosphere	Example 7: In the condition of adding magnesium turnings in situ,The boron esterification of ortho-fluorobenzyl chloride and bis-boronic acid pinacol ester catalyzed by Fe(acac)3 was followed by the addition of the catalyst (3.5 mg, 0.010 mmol, 2 molpercent) under argon atmosphere.Bis(pinacolato)boronic acid ester (127.0 mg, 0.5 mmol),Magnesium turnings (16.8 mg, 0.7 mmol), tetrahydrofuran (1 mL),After addition of o-fluorobenzyl chloride (160 μl, 1.35 mmol) at 0°C,The reaction was carried out for 3 hours, and the reaction was terminated with the addition of water. The reaction product was extracted with ethyl acetate and the yield was 82percent as calculated by gas chromatography.

Reference： [1] Patent: CN107903281, 2018, A, . Location in patent: Paragraph 0030
[2] Tetrahedron Letters, 2003, vol. 44, # 2, p. 233 - 235

2
[ 76-09-5 ]
[ 1993-03-9 ]
[ 18107-18-1 ]
[ 517920-60-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: at 60℃; for 4 h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran; 1,4-dioxane; water at 60℃; for 4 h;	To a 10 mL reaction tube equipped with a magnet was added 56 mg (0.4 mmol) of 2-fluorobenzeneboronic acid, 0.6 mL (1.2 mmol) of trimethylsilyl diazomethane (2 M n-hexane solution), 1 mL of toluene was added to the system, The rubber stopper was stoppered and reacted on an electromagnetic heating stirrer at 60 ° C for 4 hours.(0.4 mmol) of tetramethylammonium fluoride (1 M tetrahydrofuran solution) and 200 uL of water were added to an electromagnetic heating stirrer at 60 ° C On the reaction for 4 hours.After completion of the reaction, the organic solvent was removed by a rotary evaporator and purified by column chromatography2-fluorobenzyl boronic acid pinacol ester, its structure is as follows:The compound was a colorless liquid in a yield of 81percent and its NMR data was as follows:

Reference： [1] Patent: CN105884808, 2016, A, . Location in patent: Paragraph 0148; 0149; 0150; 0151; 0152; 0153

3
[ 446-48-0 ]
[ 73183-34-3 ]
[ 517920-60-4 ]

Yield	Reaction Conditions	Operation in experiment
23%	With copper(l) iodide; lithium methanolate; triphenylphosphine In N,N-dimethyl-formamide at 20℃; for 14 h; Inert atmosphere	2-Fluorobenzyl bromide (3000 mg, 15 mmol), boronic acid pinacol ester (6000 mg, 24 mmol),CuI (320 mg, 1.5 mmol), LiOMe (1200 mg, 32 mmol), PPh3 (540 mg, 2 mmol) and DMF (50 mL) were placed in a 250 mL reaction flask and replaced with nitrogen three times and then reacted for 14 h at room temperature. The reaction solution was poured into 200 mL of water, and the CuI was removed by filtration and washed three times with EA. The filtrate was collected and separated, and the aqueous extracted with EA (150 mL×3). After concentrating the EA layer, the title compound 52b (980 mg, 23percent)

Reference： [1] Angewandte Chemie - International Edition, 2012, vol. 51, # 2, p. 528 - 532
[2] Angewandte Chemie - International Edition, 2012, vol. 51, # 2, p. 528 - 532
[3] Patent: CN108341777, 2018, A, . Location in patent: Paragraph 0654-0657

4
[ 1072-85-1 ]
[ 78782-17-9 ]
[ 517920-60-4 ]

Reference： [1] Organic Letters, 2011, vol. 13, # 13, p. 3368 - 3371

[ 517920-60-4 ] Synthesis Path-Downstream 1~12

1
[ 345-35-7 ]
[ 73183-34-3 ]
[ 517920-60-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With iron(III)-acetylacetonate; magnesium; In tetrahydrofuran; at 0℃; for 3h;Inert atmosphere;	Example 7: In the condition of adding magnesium turnings in situ,The boron esterification of ortho-fluorobenzyl chloride and bis-boronic acid pinacol ester catalyzed by Fe(acac)3 was followed by the addition of the catalyst (3.5 mg, 0.010 mmol, 2 mol%) under argon atmosphere.Bis(pinacolato)boronic acid ester (127.0 mg, 0.5 mmol),Magnesium turnings (16.8 mg, 0.7 mmol), tetrahydrofuran (1 mL),After addition of o-fluorobenzyl chloride (160 mul, 1.35 mmol) at 0C,The reaction was carried out for 3 hours, and the reaction was terminated with the addition of water. The reaction product was extracted with ethyl acetate and the yield was 82% as calculated by gas chromatography.

Reference： [1]Patent: CN107903281,2018,A .Location in patent: Paragraph 0030
[2]Tetrahedron Letters,2003,vol. 44,p. 233 - 235

2
[ 1072-85-1 ]
[ 78782-17-9 ]
[ 517920-60-4 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 3368 - 3371

3
[ 446-48-0 ]
[ 73183-34-3 ]
[ 517920-60-4 ]

Yield	Reaction Conditions	Operation in experiment
40%	With 1,1'-bis-(diphenylphosphino)ferrocene; potassium acetate; palladium diacetate; In 1,4-dioxane; at 65 - 100℃; for 19h;Inert atmosphere;	General procedure: Procedure1: An oven-dried three-neck round bottom flask was fitted with a condenser. Pd(OAc)2 (145.7 mg, 0.649 mmol), dppf (359.5 mg, 0.649 mmol) bis(pinacolato)diboron (4.120 g, 16.22 mmol) and potassium acetate (1.592 g, 16.22 mmol) were added to the flask. The flask was evacuated and backfilled with argon (this process was repeated a total of 3 times). Benzyl bromide (2.000 g, 11.69 mmol) was added followed by the addition of 1,4-dioxane (30 mL). The reaction mixture was heated to 100 for 4 h and 65 for 15 h and then cooled to room temperature. The reaction mixture was passed through a plug of silica gel eluting with EtOAc and washed with saturated brine (3×50 mL). The organic layers were dried over MgSO4, concentrated in vacuo, and the residue was purified by silica gel flash chromatography.
23%	With copper(l) iodide; lithium methanolate; triphenylphosphine; In N,N-dimethyl-formamide; at 20℃; for 14h;Inert atmosphere;	2-Fluorobenzyl bromide (3000 mg, 15 mmol), boronic acid pinacol ester (6000 mg, 24 mmol),CuI (320 mg, 1.5 mmol), LiOMe (1200 mg, 32 mmol), PPh3 (540 mg, 2 mmol) and DMF (50 mL) were placed in a 250 mL reaction flask and replaced with nitrogen three times and then reacted for 14 h at room temperature. The reaction solution was poured into 200 mL of water, and the CuI was removed by filtration and washed three times with EA. The filtrate was collected and separated, and the aqueous extracted with EA (150 mL×3). After concentrating the EA layer, the title compound 52b (980 mg, 23%)
	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 80 - 90℃; for 12h;Inert atmosphere;	Compound WX068-1 (5.00 g, 26.45 mmol, 3.18 mE), bis(pinacolato)diboron (10.08 g, 39.67 mmol), tetrakis (triphenylphosphine) palladium (3.06 g, 2.64 mmol) and potassium carbonate (10.97 g, 79.35 mmol) were dissolved in dioxane (100.00 mE) at room temperature. The reaction mixture was heated to 80-90 C. for 12 hours under nitrogen atmosphere. After the reaction, the mixture was cooled to room temperature, diluted with water (200 mE) and ethylacetate (500 mE). The organic phases were separated,washed with saturated brine (100 mEx2) and dried over anhydrous sodium sulfate, followed by filtration. The filtrate was concentrated under reduced pressure to remove the solvent. The obtained residue was isolated by column chromatography (eluent: petroleum ether/ethyl acetate100/1 - 10/1, volume ratio) to obtain the target product WX068-2. ?H NMR (400 MHz, CDC13) oe: 7.28-6.93 (m, 4H), 2.26 (s, 2H), 1.25 (s, 12H).

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 528 - 532
[2]Angewandte Chemie - International Edition,2012,vol. 51,p. 528 - 532
[3]Tetrahedron Letters,2019,vol. 60,p. 1321 - 1324
[4]Patent: CN108341777,2018,A .Location in patent: Paragraph 0654-0657
[5]Patent: US2019/177318,2019,A1 .Location in patent: Paragraph 0280-0283

4
[ 517920-60-4 ]
[ 74-88-4 ]
[ 446-49-1 ]

Reference： [1]RSC Advances,2013,vol. 3,p. 9391 - 9401

5
10-bromo-9-fluoro-3-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide [ No CAS ]
[ 517920-60-4 ]
10-bromo-9-fluoro-3-[(2-fluorophenyl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 627 - 640

6
[ 2521-92-8 ]
[ 517920-60-4 ]
C₁₇H₁₇BrFNO₂ [ No CAS ]

Reference： [1]RSC Advances,2017,vol. 7,p. 16561 - 16564

7
[ 76-09-5 ]
[ 1993-03-9 ]
[ 18107-18-1 ]
[ 517920-60-4 ]

Yield	Reaction Conditions	Operation in experiment
81%		To a 10 mL reaction tube equipped with a magnet was added 56 mg (0.4 mmol) of 2-fluorobenzeneboronic acid, 0.6 mL (1.2 mmol) of trimethylsilyl diazomethane (2 M n-hexane solution), 1 mL of toluene was added to the system, The rubber stopper was stoppered and reacted on an electromagnetic heating stirrer at 60 C for 4 hours.(0.4 mmol) of tetramethylammonium fluoride (1 M tetrahydrofuran solution) and 200 uL of water were added to an electromagnetic heating stirrer at 60 C On the reaction for 4 hours.After completion of the reaction, the organic solvent was removed by a rotary evaporator and purified by column chromatography2-fluorobenzyl boronic acid pinacol ester, its structure is as follows:The compound was a colorless liquid in a yield of 81% and its NMR data was as follows:

Reference： [1]Patent: CN105884808,2016,A .Location in patent: Paragraph 0148; 0149; 0150; 0151; 0152; 0153

8
[ 517920-60-4 ]
methyl 7-(2-fluorobenzyl)-4-hydroxy-1-methylisoquinoline-3-carboxylate [ No CAS ]

Reference： [1]Patent: CN108341777,2018,A

9
[ 517920-60-4 ]
2-(7-(2-fluorobenzyl)-4-hydroxy-1-methylisoquinoline-3-carboxamido)acetic acid [ No CAS ]

Reference： [1]Patent: CN108341777,2018,A

10
methyl 4-benzyloxy-1-methyl-7-bromoisoquinoline-3-carboxylate [ No CAS ]
[ 517920-60-4 ]
methyl 4-(benzyloxy)-7-(2-fluorobenzyl)-1-methylisoquinoline-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With palladium diacetate; potassium carbonate; catacxium A; In water; for 12h;Inert atmosphere; Heating;	<strong>[517920-60-4]2-fluorobenzylboronic acid pinacol ester</strong> (980 mg, 3.66 mmol),Methyl 4-(benzyloxy)-7-bromo-1-methylisoquinoline-3-carboxylate (716 mg, 1.8 mmol), Pd(OAc) 2 (90 mg, 0.4 mmol), Cata CXium A (258 mg, 0.7 Methyl), K2CO3 (760 mg, 5.5 mmol) and 1,4-dioxane/water (20 mL/4 mL) were sequentially added to a 100 mL reaction flask, and the reaction solution was replaced with nitrogen three times and then heated to 70 C for 12 h, TLC monitoring The reaction to the starting material is complete. The reaction solution was poured into water to quench the reaction, which was extracted with EA (120 mL×3). The title compound 52d (520 mg, 68%).

Reference： [1]Patent: CN108341777,2018,A .Location in patent: Paragraph 0654; 0655; 0658; 0659

11
[ 254454-54-1 ]
[ 517920-60-4 ]
tert-butyl 2-(2-fluorobenzyl)azetidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With dichloro(1,5-cyclooctadiene)palladium(II); tetrabutylammomium bromide; caesium carbonate; ruphos; In 1,4-dioxane; water; at 80℃; for 24h;Inert atmosphere;	General procedure: General Procedure: A glass test tube, which was equipped with a magnetic stir bar and fitted with a stopper, was charged with Pd(COD)Cl2 (14.3 mg, 0.05 mmol) and RuPhos (46.7 mg, 0.10 mmol). Cs2CO3 (488.7 mg, 1.5 mmol, 3.0 equiv.), benzylboronic acid pinacol ester (1.0 mmol, 2.0 equiv.), N-Boc-3-iodo-azetidine (283.1 mg, 0.5 mmol, 1.0 equiv.) and 3 mL 1,4-dioxane/H2O (1:1). The reaction mixture was purged with argon gas three times. Under argon, the reaction mixture was allowed to stir at 80 oC for 24 h. The progress of the reaction was monitored by GC-MS. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (15 mL) and washed with saturated brine (3×10 mL). The aqueous layer was extracted with ethyl acetate (2×15 mL). The combined organic layers were dried over MgSO4, concentrated in vacuo, and purified by silica gel flash chromatography.

Reference： [1]Tetrahedron Letters,2019,vol. 60,p. 1321 - 1324

12
3-nitro-2,4-dibromopyridine [ No CAS ]
[ 517920-60-4 ]
C₁₂H₈BrFN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 80℃; for 12h;Inert atmosphere;	Compound WX068-4 (3.50 g, 12.42 mmol), [1,1?- bis(diphenylphosphino)ferrocene]palladium dichloride dichloromethane complex (1.38 g, 1.69 mmol) and potassium carbonate (4.68 g, 33.89 mmol) were dissolved in dioxane (100.00 mE) and water (30.00 mE) at room temperature. The reaction mixture was heated to 80 C. and stirred for 12 hours under nitrogen atmosphere. After the reaction, the mixture was cooled to room temperature, filtered by diatomite and diluted with ethyl acetate (500 mE) and water (100 mE). The organic phases were separated, wash with saturated brine (100 mEx2) and dried over anhydrous sodium sulfate, followed by filtration. The filtrate was concentrated under reduced pressure to remove the solvent. The obtained residue was isolated by preparative HPEC to obtain the target product WX068-5. MS-ESI mlz:310.8 [M+H], 312.8 [M+H+2]. ?H NMR (400 MHz, CDC13) oe: 8.28 (d, J=5.0 Hz, 1H), 7.28-7.17 (m, 1H), 7.11-6.97 (m, 4H), 3.92 (s, 2H).

Reference： [1]Patent: US2019/177318,2019,A1 .Location in patent: Paragraph 0280-0281; 0289-0290

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Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Complex Metal Hydride Reductions • Ester Cleavage • Friedel-Crafts Reaction • Hydrogenolysis of Benzyl Ether • Preparation of Alkylbenzene • Reactions of Benzene and Substituted Benzenes • Reactions with Organometallic Reagents • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Vilsmeier-Haack Reaction

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H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 517920-60-4 ] 2-(2-Fluorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Quality Control of [ 517920-60-4 ]

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Application In Synthesis of [ 517920-60-4 ]

[ 517920-60-4 ] Synthesis Path-Upstream 1~4

[ 517920-60-4 ] Synthesis Path-Downstream 1~12

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