Methanesulfonyl chloride → 3-Acetamido-6-chloro-2-fluorobenzyl methanesulfonate

HRID 1430449Notes

Reaction equation

HRID 1430449 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:11])[CH3:10])=[C:4]([F:12])[C:3]=1[CH2:13][OH:14].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[CH3:15][S:16]([O:14][CH2:13][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[C:5]([NH:8][C:9](=[O:11])[CH3:10])[C:4]=1[F:12])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 86713625N-(4-chloro-2-fluoro-3-(hydroxymethyl)phenyl)acetamide

Product 1

HCID 867136263-Acetamido-6-chloro-2-fluorobenzyl methanesulfonateYield 91.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 0° C. of N-(4-chloro-2-fluoro-3-(hydroxymethyl)phenyl)acetamide (1.05 g, 4.82 mmol) and TEA (1.003 mL, 7.24 mmol) in DCM (30 mL) was treated slowly with methanesulfonyl chloride (0.414 mL, 5.31 mmol), warmed to RT and stirred for 2 h. The mixture was treated with satd. NaHCO3, extracted with DCM (2×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford 3-acetamido-6-chloro-2-fluorobenzyl methanesulfonate (1.31 g, 74% yield) as an off-white solid. MS (ESI) m/z: 296.0 [M+H]+.

Workup

  1. additionThe mixture was treated with satd
  2. extractionNaHCO3, extracted with DCM (2×)
  3. washthe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a61b109aba2a4179a1f8a668c152d659
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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