Boron tribromide → 2-Fluoro-4-methylsulfonylphenol

HRID 2246235Notes

Reaction equation

HRID 2246235 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:12]C.B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[OH:12]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 56971745HCID 56971745, compound

Product 1

HCID 161288422-Fluoro-4-methylsulfonylphenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of the product from Step B (480 mg, 2.35 mmol) in dichloromethane (10 mL) was added boron tribromide (12.0 mL, 1.0 M in dichloromethane, 12.0 mmol) at −78° C. The reaction was then allowed to warm to room temperature slowly. After stirring at room temperature for 12 h, the reaction was concentrated under reduced pressure and the residue was purified by flash chromatography (silica gel, 50:50 hexanes/ethyl acetate) to give the desired compound.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography (silica gel, 50:50 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-639d8a78b50149e7b7ca000b8d9c11dc
Source dataset
uspto-grants-2010_03
Patent number
US07687492B2

Reaction notes

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