232275-53-5|Methyl 4-bromo-2,6-dichlorobenzoate| Ambeed

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Quality Control of [ 232275-53-5 ] Purity: 98% SDS Specification

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Product Details of [ 232275-53-5 ]

CAS No. :	232275-53-5
Formula :	C₈H₅BrCl₂O₂
M.W :	283.93
SMILES Code :	O=C(OC)C1=C(Cl)C=C(Br)C=C1Cl
MDL No. :	MFCD28037387
Boiling Point :	No data available
InChI Key :	JEOFIYOVYSTDJH-UHFFFAOYSA-N
Pubchem ID :	53951230

Safety of [ 232275-53-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319
Precautionary Statements:	P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362

Application In Synthesis of [ 232275-53-5 ]

* 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 [ 232275-53-5 ]

[ 232275-53-5 ] Synthesis Path-Downstream 1~35

1
[ 232275-53-5 ]
[ 232275-51-3 ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2051 - 2066.

2
[ 232275-49-9 ]
[ 232275-53-5 ]

Yield	Reaction Conditions	Operation in experiment
	With copper; sodium nitrite; In aq. HBr;	1) 4-Amino-2,6-dichlorobenzoic acid methyl ester (1.00 g) was suspended in 40% aq. HBr and the mixture was cooled 1 to 0-5 C. After NaNO2 (376 mg) was added in small portions, the mixture was stirred for about 5 min. Copper (100 mg) was added and the mixture was warmed up to 100 C. The mixture was then stirred at 100 C. for 30 min, diluted with water and extracted with AcOEt. The extract was dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (silica gel; eluent: hexane and AcOEt 50:1) to give 4-bromo-2,6-dichlorobenzoic acid methyl ester (1.07 g).

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2051 - 2066.
[2]Patent: US6521666,2003,B1 .

3
[ 22509-50-8 ]
[ 232275-53-5 ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2051 - 2066.

4
[ 232275-50-2 ]
[ 232275-53-5 ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2051 - 2066.

5
[ 232275-53-5 ]
4-bromo-2,6-dichlorobenzoyl chloride [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2051 - 2066.

6
[ 88135-16-4 ]
[ 232275-53-5 ]

References: [1]Bioorganic and Medicinal Chemistry,2002,vol. 10,p. 2051 - 2066.

7
[ 232275-53-5 ]
[ 98-80-6 ]
[ 232275-78-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;Pd(PPh3)4; In tetrahydrofuran; hexane; ethyl acetate;	1) To a solution of 2,6-dichloro-4-bromobenzoic acid methyl ester (0.55 g) in THF (10 mL) was added benzeneboronic acid (1.30 g), Pd(PPh3)4 (0.16 g) and 2M Na2CO3 (5 mL). The mixture was refluxed for 4 h under N2. After cooling, the mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by preparative TLC (silica gel; eluent: hexane to EtOAc/hexane 1/1) to yield crude 2,6-dichloro-4-phenylbenzoic acid methyl ester (0.57 g). ESMS: m/z 281 (MH+).

References: [1]Patent: US6521666,2003,B1 .

8
[ 99-99-0 ]
C₈H₄Br₂Cl₂O₂ [ No CAS ]
[ 232275-53-5 ]

References: [1]Patent: CN104341316,2017,B .

9
[ 7149-69-1 ]
C₈H₄Br₂Cl₂O₂ [ No CAS ]
[ 232275-53-5 ]

References: [1]Patent: CN104341316,2017,B .

10
[ 22509-50-8 ]
C₈H₄Br₂Cl₂O₂ [ No CAS ]
[ 232275-53-5 ]

References: [1]Patent: CN104341316,2017,B .

11
[ 232275-49-9 ]
C₈H₄Br₂Cl₂O₂ [ No CAS ]
[ 232275-53-5 ]

Yield	Reaction Conditions	Operation in experiment
		Take the crude compound obtained from the previous step (220 mg, lmmol) was added to 48% hydrobromic acid (20 mL), dissolved in a slight heat, and then cooled to a temperature range of -10 to 5 C. A white powder was precipitated and the sodium nitrite (76 mg, 1. Lmmol) and the reaction temperature was controlled below -5 C during the addition. After adding, the mixture was stirred for 1 h, then the cuprous bromide powder (144 mg, lmmol) was added. After the addition, the temperature was gradually raised to the reflux temperature and reacted at reflux temperature for 1 to 2 hours. After the end of the reaction, the ethyl acetate was extracted and the organic layer was washed with saturated sodium carbonate, washed with brine, dried over anhydrous sodium sulfate and separated by column chromatography to obtain a monobromine and bisbromide mixture (150 mg). The silica gel column was difficult to separate

References: [1]Patent: CN104341316,2017,B .Location in patent: Paragraph 0352; 0356.

12
[ 13737-05-8 ]
[ 232275-53-5 ]
2,6-dichloro-4-(pyridin-2-yl)benzaldehyde [ No CAS ]
2-chloro-4-(pyridin-2-yl)benzaldehyde [ No CAS ]

References: [1]Patent: WO2018/145021,2018,A1 .

13
[ 13737-05-8 ]
[ 232275-53-5 ]
methyl 2,6-dichloro-4-(pyridin-2-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47.5%	With tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 20 - 100℃; for 66.0h;Sealed tube; Inert atmosphere;	In a sealed tube, <strong>[232275-53-5]methyl 4-bromo-2,6-dichlorobenzoate</strong>both (3.18 g,11.2 mmol) and 2-(trimethylstannyl)pyridine (1.94 ml, 11.2 mmol) and tetrakis(triphenyl phosphine)palladium (647.1 mg, 0.56 mmol) are suspended in DMF (25 mL). The mixture was degased with argon for 10 mm heated to 100 C for 18 hours, and then at room temperature. After 48 h the reaction was diluted with EtOAc and washed with KF (3 g in 50 mL water) andbrine (3x) and dried over Na2504, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (0% to 20% EtOAc/ hexanes) to afford methyl 2,6-dichloro-4-(pyridin-2-yl)benzoate (1.5 g, 47.5%). This material was dissolved in THF (25mL), cooled to 0 C, then lithium aluminum hydride (0.4 g, 10.63 mmol) was added slowly, after the addition was completed, the reaction mixture was warmed up slowly to roomtemperature and stirred for 1 h, then cooled back to 0 C added water (500 uL) slowly (vigorous gas evolution), followed by NaOH (2 M, 500 uL) then water (1500 uL). The slurry was stirred at room temperature. After 1 h, Na2504 was added, and then the mixture was filtered through Celite. The solid was rinsed with Et20 (200 mL), and the filtrate was concentrated under reduced pressure, the residue was diluted with EtOAc and washed with water then dried overNa2504, filtered and concentrated under reduced pressure. The cmde residue (1.5 g, 5.9 mmol) was combined with pyridinium chlorochromate (1.91 g, 8.85 mmol) and Celite (700 mg, 7mmol), DCM (10 mL) was added and the reaction mixture was stirred at room temperature for 48 h. The reaction was filtered through a Celite frit with a small plug of silica, and rinsed several times with DCM/EtOAc, and then the filtrate was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography toafford P24 (392 mg, 26.3%). MS (ESI) mlz 252.0 [M+Hj . 1H NMR (400 MHz, Chloroformd) ö 10.54 (s, 1H), 8.74 (ddd, J = 4.8, 1.8, 0.9 Hz, 1H), 8.06 (s, 2H), 7.83 (ddd, J = 8.0, 7.4, 1.8 Hz, 1H), 7.77 (dt, J = 8.0, 1.1 Hz, 1H), 7.36 (ddd, J = 7.4, 4.8, 1.2 Hz, 1H) and P25 (195 mg, 15.2%). MS (ESI) m/z 218.1 [M+Hj . 1H NMR (400 MHz, Chloroform-d) ö 10.52 (d, J = 0.8 Hz, 1H), 8.74 (ddd, J = 4.8, 1.7, 1.0 Hz, 1H), 8.17 (dd, J = 1.6, 0.5 Hz, 1H), 8.07 - 7.95 (m, 2H),7.91 - 7.75 (m, 2H), 7.39 - 7.29 (m, 1H).

References: [1]Patent: WO2018/145021,2018,A1 .Location in patent: Page/Page column 80; 81.

14
[ 232275-51-3 ]
[ 74-88-4 ]
[ 232275-53-5 ]

Yield	Reaction Conditions	Operation in experiment
98.10%	With potassium carbonate; In acetonitrile; at 20℃; for 16.0h;	General procedure: To a 100 mL 1-neck round bottom flask, the mixture of 4-bromo-2,6-dichloro-benzoic acid (500 mg, 1.85 mmol), iodomethane (788.82 mg, 5.56 mmol, 345.97 uL), Potassium carbonate (1.28 g, 9.26 mmol, 559.01 uL) in acetonitrile (20 mL) was stirred at RT for 6 h, then it was diluted with water, extracted with EA, dried with Na2SO4, concentrated to afford methyl 4-bromo-2,6-dichloro-benzoate (516 mg, 1.82 mmol, 98.10% yield) as yellow oil, it was used to next step without further purification. 1H NMR (400 MHz, CDCl3) δ 7.51 (s, 2H), 3.97 (s, 3H).
95.06%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃;	To a solution of 0190-1 (2.00 g, 7.41 mmol) and CI (1.05 g, 7.41 mmol) in DMF (5 mL), was added K2CO3 (1.54 g, 11.11 mmol) and the mixture was stirred at room temperature for overnight. After the reaction was finished, water was added and the mixture was filtered and the liquid layer was extracted with EA (20 mL x 3), the organic phase was combined and washed with water then brine, dried over Na2SC>4, concentrated and purified by prep-HPLC to get 0190-2 (2.0 g, 95.06% yield) as a white solid. Agilent LCMS 1200-6120, Column: Halo Cl 8 (30 mm4.6 mm2.7 pm); Column Temperature: 40 C; Flow Rate: 3.0 mL/min; Mobile Phase: from 95% [water + 10 mM TFA] and 5% [CH3CN] to 0% [water + 10 mM TFA] and 100% [CH3CN] in 0.8 min, then under this condition for 0.4 min, finally changed to 95% [water + 10 mM TFA] and 5% [CH3CN] in 0.01 min. Purity is 93.35%. Rt = 0.853 min; MS Calcd.:282.7; MS Found: 283.7 [M+H]+.

References: [1]Patent: US2021/171455,2021,A1 .Location in patent: Paragraph 0759; 0915-0917; 0927-0929; 0977-0979.
[2]Patent: WO2021/222789,2021,A1 .Location in patent: Paragraph 0724; 1091-1093; 1126-1128.

15
[ 232275-53-5 ]
2,6-dichloro-4-morpholinobenzoic acid [ No CAS ]

References: [1]Patent: US2021/171455,2021,A1 .

16
[ 232275-53-5 ]
(2 S)-2-(2,6-dichloro-4-morpholinobenzamido)-3-(2-(3-(5-fluoro-1,4,5,6-tetrahydropyrimidin-2-ylamino)benzamido)acetamido)propanoic acid [ No CAS ]

References: [1]Patent: US2021/171455,2021,A1 .

17
[ 232275-53-5 ]
2,6-dichloro-4-(1,1-dioxo-1,4-thiazinan-4-yl)benzoic acid [ No CAS ]

References: [1]Patent: US2021/171455,2021,A1 .

18
[ 232275-53-5 ]
C₂₇H₃₀Cl₂FN₇O₇S [ No CAS ]

References: [1]Patent: US2021/171455,2021,A1 .

19
[ 39093-93-1 ]
[ 232275-53-5 ]
methyl 2,6-dichloro-4-(1,1-dioxo-1,4-thiazinan-4-yl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75.56%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃;Inert atmosphere; Sealed tube;	Methyl 4-bromo-2,6-dichloro-benzoate (70 mg, 246.54 umol), 1,4-thiazinanel,1-dioxide hydrochloride (50.78 mg, 295.84 umol), diacetoxypalladium (2.77 mg, 12.33 umol), binap (9.21 mg, 14.79 umol), Cesium carbonate (240.98 mg, 739.61 umol) in toluene (5 mL) was added to a nitrogen-filled sealed tube, and the subsequent reaction mixture was stirred at 100 C. overnight, TLC showed that the starting material was consumed, then the reaction mixture was diluted with DCM, and filtered to collect the filtrate. The crude material was purified by silica gel column (PE:EA=4:1) to afford methyl 2,6-dichloro-4-(1,1-dioxo-1,4-thiazinan-4-yl)benzoate (63 mg, 186.28 umol, 75.56% yield) LC-MS (Agilent LCMS 1260-6120, Column: Waters X-Bridge C18 (50 mm4.6 mm3.5 μm); Column Temperature: 40 C.; Flow Rate: 1.5 mL/min; Mobile Phase: from 95% [water+10 MmNH4HCO3] and 5% [CH3CN] to 5% [water+10 MmNH4HCO3] and 95% [CH3CN] in 2 min, then under this condition for 2 min. Purity is 100%. Rt=2.362 min; MS Calcd.: 337.0; MS Found: 337.8 [M+H]+. 1H NMR (400 MHz, CDCl3) δ 6.80 (s, 2H), 3.95 (s, 3H), 3.92-3.85 (m, 4H), 3.13-3.05 (m, 4H).

References: [1]Patent: US2021/171455,2021,A1 .Location in patent: Paragraph 0759; 0927; 0930-0932.

20
[ 110-91-8 ]
[ 232275-53-5 ]
methyl 2,6-dichloro-4-morpholinobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.18%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 100℃;Inert atmosphere; Sealed tube;	Methyl 4-bromo-2,6-dichloro-benzoate (200 mg, 704.39 umol), diacetoxypalladium (7.91 mg, 35.22 umol), Binap (26.32 mg, 42.26 umol), Cesium carbonate (688.51 mg, 2.11 mmol), morpholine (92.05 mg, 1.06 mmol, 92.42 uL) in toluene (5 mL) were added to a nitrogen-filled high-pressure sealed tube, and it was stirred at 100 C. overnight, TLC demonstrated that the starting material was consumed, then the reaction mixture was diluted with DCM, and it was filtered to collect the filtrate, purified by silica gel column (PE:EA=10:1) to afford methyl 2,6-dichloro-4-morpholino-benzoate (170 mg, 585.92 umol, 83.18% yield) as white powder.

References: [1]Patent: US2021/171455,2021,A1 .Location in patent: Paragraph 0759; 0915; 0918-0920; 0977; 0981-0982.

21
[ 232275-53-5 ]
methyl 2,6-dichloro-4-phenethoxybenzoate [ No CAS ]