Triethylamine → 4-Bromo-2-chlorobenzyl methanesulfonate

HRID 1828798Notes

Reaction equation

HRID 1828798 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 added dropwise methanesulfonyl chloride (1.4 ml) under ice-cooling in a nitrogen atmosphere. The mixture was stirred for 1 hr, and the reaction mixture was washed with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The filtrate was concentrated to give 4-bromo-2-chloro-1-((methanesulfonyloxy)-methyl)benzene as a pale-brown solid (4.77 g).

Workup

  1. temperaturecooling in a nitrogen atmosphere
  2. washthe reaction mixture was washed with water, saturated aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4aa4643bf50f4c25be47a1f1df94a7f0
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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