2-Bromo-1-(4-hydroxyphenyl)ethanone → HCID 13654483, compound

HRID 1091369Notes

Reaction equation

HRID 1091369 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Br:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)=[O:9].C(N(CC)CC)C>O1CCCC1>[CH3:1][S:2]([O:16][C:13]1[CH:14]=[CH:15][C:10]([C:8](=[O:9])[CH2:7][Br:6])=[CH:11][CH:12]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 49642-Bromo-1-(4-hydroxyphenyl)ethanoneHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 13654483HCID 13654483, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (50 g, 436 mmol) was added to a solution of 2-bromo-1-(4-hydroxyphenyl)-ethan-1-one (85 g, 395 mmol) and triethylamine (48 g, 474 mmol) in tetrahydrofuran (1000 ml) at 0° C. and the mixture was stirred for 30 minutes at room temperature. The mixture was partitioned between water and ethyl acetate, and the organic layer was washed with brine, dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was washed with diisopropyl ether to afford 4-(2-bromoacetyl)phenyl methanesulfonate (96 g, 83%) as white crystals.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-f350e8bd034344a08ba316e657134e29
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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