Methanesulfonyl chloride → N-(5-bromo-2-fluorobenzyl)methanesulfonamide

HRID 606816Notes

Reaction equation

HRID 606816 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[CH:5][C:6]([F:11])=[C:7]([CH:10]=1)[CH2:8][NH2:9].C(N(C(C)C)CC)(C)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>ClCCl.C(OCC)(=O)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([F:11])=[C:7]([CH:10]=1)[CH2:8][NH:9][S:22]([CH3:21])(=[O:24])=[O:23]

Participants

6

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 27249035-Bromo-2-fluorobenzylamine hydrochloride

Product 1

HCID 40161431N-(5-bromo-2-fluorobenzyl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 5-bromo-2-fluorobenzylamine hydrochloride (500 mg, 2.08 mmol) in dichloromethane (8 mL) and diisopropylethylamine (0.90 mL, 5.20 mmol) and treat with methanesulfonyl chloride (0.19 mL, 2.49 mmol). After 4.5 h dilute with ethyl acetate and wash with 0.5 N hydrochloric acid, an aqueous saturated solution of sodium bicarbonate, and an aqueous saturated solution of sodium chloride. Dry (sodium sulfate), filter, and concentrate to give the title compound as a pale orange oil, which crystallizes upon standing (573 mg, 98%).

Workup

  1. washwash with 0.5 N hydrochloric acid
  2. dry with materialDry (sodium sulfate)
  3. filtrationfilter
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-e0a0aca20b13410f8bbf34abf9a01e2f
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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