Boron tribromide → 1-[2-Hydroxy-4-(methylthio)phenyl]ethanone

HRID 39030Notes

Reaction equation

HRID 39030 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[C:11]([S:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C:15](=[O:17])[CH3:16]>C(Cl)Cl>[OH:6][C:7]1[CH:12]=[C:11]([S:13][CH3:14])[CH:10]=[CH:9][C:8]=1[C:15](=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 13578023Ethanone, 1-[2-methoxy-4-(methylthio)phenyl]-

Product 1

HCID 668786661-[2-Hydroxy-4-(methylthio)phenyl]ethanoneYield 97.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (19 ml, 1 N in DCM, 19 mmol) was added to a mixture of crude 1-[2-methoxy-4-(methylthio)phenyl]ethanone (3.6 g, 16.9 mmol) and DCM (25 ml) at 0° C. The mixture was brought to room temperature and stirred for 3 h. Ice/water was added, the organic phase was separated and the water phase was extracted with EtOAc. The combined organic phases were filtered through a short plug of silica (EtOAc) and were concentrated to give the title compound (3.0 g) MS m/z (rel. intensity, 70 eV) 183 (6), 182 (M+, 53), 168 (10), 167 (bp), 152 (6).

Workup

  1. customwas brought to room temperature
  2. customthe organic phase was separated
  3. extractionthe water phase was extracted with EtOAc
  4. filtrationThe combined organic phases were filtered through a short plug of silica (EtOAc)
  5. concentrationwere concentrated

Sources & evidence

ORD record
ord-7243f6522fda490f90dfef429367cc2e
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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