Boron tribromide → 2,3-Difluoro-4-methyl-5-nitro-phenol
Reaction equation
COC(=O)[O:4][C:5]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[C:8]([CH3:14])=[C:7]([F:15])[C:6]=1[F:16].B(Br)(Br)Br>ClCCl>[F:16][C:6]1[C:7]([F:15])=[C:8]([CH3:14])[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:5]=1[OH:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of carbonic acid 2,3-difluoro-4-methyl-5-nitro-phenyl ester methyl ester (2.3 g, 9.3 mmol) in dichloromethane (30 ml) was cooled to 0° C. in an ice bath, and 1.0M boron tribromide in dichloromethane (9.3 ml, 9.3 mmol) was added. The ice-bath was removed and the mixture was stirred at room temperature for 18 hours. Water was added and the mixture was extracted with EtOAc. The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 9:1) gave 1.02 g (58%) of 2,3-difluoro-4-methyl-5-nitro-phenol as a white solid.