ChemicalBook CAS DataBase List 2-BROMO-3-FLUOROBENZALDEHYDE

2-BROMO-3-FLUOROBENZALDEHYDE synthesis

5synthesis methods

Product Name:2-BROMO-3-FLUOROBENZALDEHYDE
CAS Number:149947-15-9
Molecular formula:C7H4BrFO
Molecular Weight:203.01

261723-32-4

149947-15-9

General procedure for the synthesis of 3-bromo-2-fluorobenzaldehyde from (3-bromo-2-fluorophenyl)methanol: Manganese dioxide (9.32 g, 107.31 mmol) was added to a solution of dichloromethane (50 mL) containing (3-bromo-2-fluorophenyl)methanol (2.750 g, 13.413 mmol). The reaction mixture was stirred at 45°C overnight. Upon completion of the reaction, the mixture was filtered through diatomaceous earth and the filter cake was washed with dichloromethane. The filtrate was collected and concentrated under reduced pressure to give 3-bromo-2-fluorobenzaldehyde as a white solid (2.24 g, 83% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ10.19 (dt, J=1.3,0.7 Hz, 1H), 8.05 (tdd, J=6.8,3.1,1.5 Hz, 1H), 7.85 (ddt, J=7.9,6.4,1.5 Hz, 1H), 7.37 (tdt, J=7.8,1.6, 1H). 0.8 Hz, 1H).

261723-32-4 Synthesis

261723-32-4
144 suppliers
$10.00/1g

149947-15-9
172 suppliers
$6.00/1g

Yield:149947-15-9 83%

Reaction Conditions:

with manganese(IV) oxide in dichloromethane at 45;

Steps:

21.20.1 Example 21.20
To a solution of (3-bromo-2-fluoro-phenyl)methanol (2.750 g, 13.413 mmol) in dichloromethane (50 mL) was added manganese dioxide (9.32 g, 107.31 mmol) and the resulting mixture was stirred at 45°C overnight. Once complete, the reaction was filtered through diatomaceous earth and washed with dichloromethane to obtain 3-bromo-2-fluoro-benzaldehyde as a white solid (2.24 g, 83%). ^lU NMR (400 MHz, DMSO-i ) δ 10.19 (dt, = 1.3, 0.7 Hz, 1H), 8.05 (tdd, = 6.8, 3.1, 1.5 Hz, 1H), 7.85 (ddt, = 7.9, 6.4, 1.5 Hz, 1H), 7.37 (tdt, = 7.8, 1.6, 0.8 Hz, 1H).

References:

F. HOFFMANN-LA ROCHE AG;GENENTECH, INC.;YU, Jiang;WU, Guosheng;YUEN, Po-Wai;VILLEMURE, Elisia;SCHWARZ, Jacob;LY, Cuong;SELLERS, Benjamin;VOLGRAF, Matthew WO2015/52226, 2015, A1 Location in patent:Paragraph 0379

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1072-85-1 Synthesis