Triethylamine → 2-Bromo-5-chlorophenethyl methanesulfonate

HRID 1519138Notes

Reaction equation

HRID 1519138 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH2:9][CH2:10][OH:11].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH3:19][S:20]([O:11][CH2:10][CH2:9][C:3]1[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=1[Br:1])(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 582220262-(2-Bromo-5-chlorophenyl)ethanol

Product 1

HCID 867240582-Bromo-5-chlorophenethyl methanesulfonateYield 96.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(2-bromo-5-chloro-phenyl)ethanol (1.65 g, 7.00 mmol) [as prepared in preparation 6] and triethylamine (922 mg, 1.27 mL, 9.11 mmol) in DCM (20 mL) was cooled to 0° C. and methanesulfonyl chloride (883 mg, 597 μL, 7.71 mmol) was added. The mixture was stirred for 2 h and then diluted with DCM and washed sequentially with water and brine, the organic layer dried (MgSO4) and concentrated to afford 2-bromo-5-chlorophenethyl methanesulfonate as a yellow solid (2.11 g, 96%). 1H NMR (500 MHz, d6-DMSO) δ 7.67 (1H, d), 7.55 (1H, s), 7.32 (1H, d), 4.44 (2H, t), 3.13-3.36 (5H, m).

Workup

  1. washwashed sequentially with water and brine
  2. dry with materialthe organic layer dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b38016df0b6d472b865f2a18d8c04068
Source dataset
uspto-grants-2015_07
Patent number
US09073875B2

Reaction notes

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