Boron tribromide → 3',5-Difluoro-4'-(phenylsulfonyl)biphenyl-2-ol

HRID 1963665Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[O:24]C)[CH:5]=[CH:6][C:7]=1[S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9].B(Br)(Br)Br>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:17]2[C:18]([OH:24])=[CH:19][CH:20]=[C:21]([F:23])[CH:22]=2)[CH:5]=[CH:6][C:7]=1[S:8]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)(=[O:10])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

The product from step ii) (0.44 g) was treated with 1.0M boron tribromide in DCM (3.7 ml) in DCM (10 ml) and stirred at 0° C. for 18 h. The mixture was quenched in ice water and extracted with EtOAc; dried (MgSO4) and concentrated in vacuo to give the sub-title compound, yield 0.39 g.

Workup

customThe mixture was quenched in ice water
extractionextracted with EtOAc
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-17e8aec6de07449fa8be2687d4cac51b
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415394B2

Reaction notes

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