Triethylamine → N-(2-bromoethyl)-4-fluorobenzenesulfonamide

HRID 1992350Notes

Reaction equation

HRID 1992350 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br.[Br:13][CH2:14][CH2:15][NH2:16].C(N(CC)CC)C>ClCCl.O>[Br:13][CH2:14][CH2:15][NH:16][S:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)(=[O:10])=[O:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 2779738N-(2-bromoethyl)-4-fluorobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-Fluoro benzene sulfonyl chloride (8 g, 0.0411 mol) was added dropwise at 0° C. to a solution of 2-bromoethylamine hydrogen bromide (10.27 g, 0.0501 mol) and triethyl amine (14.3 ml, 0.1029 mol) in dry dichloromethane (100 ml) and stirred at room temperature for 1 h under nitrogen atmosphere. The reaction mixture was diluted with water and extracted with ethyl acetate. Organic layer was washed with water and brine and dried over sodium sulfate. Solvent evaporation under reduced pressure afforded the sub-title product as a liquid. Yield: 11 g

Workup

  1. extractionextracted with ethyl acetate
  2. washOrganic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-6c84479aa6cf4876b0bc149ae09b6f2a
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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