Dichloromethane → Benzeneacetic acid, 2,6-difluoro-4-hydroxy-, methyl ester
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8]C)[CH:5]=[C:4]([F:10])[C:3]=1[CH2:11][C:12]([OH:14])=[O:13].B(Br)(Br)Br.Cl[CH2:20]Cl>>[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([F:10])[C:3]=1[CH2:11][C:12]([O:14][CH3:20])=[O:13]Participants
4
Procedure
To a stirred solution of (2,6-difluoro-4-methoxyphenyl)acetic acid (1.50 g, 7.42 mmol) in 20 ml anhydrous dichloromethane at 0° C. was added a solution of boron tribromide (4.29 ml, 44.5 mmol) in 10 ml anhydrous dichloromethane. The cooling bath was removed and the mixture allowed to warm to RT for 2 hours. The reaction was diluted with 20 ml anhydrous methanol, and stirred for 30 minutes. The mixture was concentrated under reduced pressure, and the residue purified by column chromatography on silica gel, (Biotage column, 50 g) using a gradient eluent of 0-30% ethyl acetate in hexanes (700 ml) to afford the title compound. 1H NMR (CDCl3): δ 6.30 (d, J=8.3 Hz, 2H), 6.12 (br, 1H), 3.76 (s, 3H), 3.63 (s, 2H).
Workup
- customThe cooling bath was removed
- additionThe reaction was diluted with 20 ml anhydrous methanol
- concentrationThe mixture was concentrated under reduced pressure
- customthe residue purified by column chromatography on silica gel, (Biotage column, 50 g)
Sources & evidence
- ORD record
- ord-b9a8b9c3000b42259b648604ce95a09a
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018224B2
Reaction notes
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