Triethylamine → 4-Bromo-2-chlorobenzyl methanesulfonate

HRID 1072795Notes

Reaction equation

HRID 1072795 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[C:4]([Cl:10])[CH:3]=1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>ClCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][S:19]([CH3:18])(=[O:21])=[O:20])=[C:4]([Cl:10])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 43805739(4-Bromo-2-chlorophenyl)methanol

Product 1

HCID 220586494-Bromo-2-chlorobenzyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-chlorobenzyl alcohol (3.56 g) and anhydrous triethylamine (3 ml) in anhydrous dichloromethane (36 ml) was dropwise added methanesulfonyl chloride (1.4 ml) under a nitrogen atmosphere and ice-cooling. The reaction mixture was stirred for 1 hr, washed with water, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The filtrate was concentrated to give the objective compound (4.77 g) as a light brown solid.

Workup

  1. temperatureice-cooling
  2. washwashed with water
  3. dry with materiala saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-e9ea002048984dc8a307a503c020fd6d
Source dataset
uspto-grants-2005_06
Patent number
US06911469B2

Reaction notes

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