Dimethylamine → 4-bromo-2-fluoro-N,N-dimethylbenzenesulfonamide

HRID 39187Notes

Reaction equation

HRID 39187 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[C:4]([F:12])[CH:3]=1.C[CH2:14][N:15](CC)[CH2:16]C.CNC.C1COCC1>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:15]([CH3:16])[CH3:14])(=[O:10])=[O:9])=[C:4]([F:12])[CH:3]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 27363104-Bromo-2-fluorobenzene-1-sulfonyl chloride

Product 1

HCID 592067474-bromo-2-fluoro-N,N-dimethylbenzenesulfonamideYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-bromo-2-fluorobenzene-1-sulfonyl chloride (1.0 g, 3.7 mmol) and Et3N (1.5 mL, 11 mmol) in dichloromethane (10 mL) was added a solution of dimethylamine 2.0 M in THF (2.2 mL, 4.4 mmol). The reaction was stirred at ambient temperature for 30 minutes. The reaction was washed with 10 mL of 1N aqueous HCl and 10 mL of brine. Organics were dried over Na2SO4 and evaporated to dryness. Crude product was purified by chromatography on silica gel (eluting with 0-25% ethyl acetate in hexanes) to afford 4-bromo-2-fluoro-N,N-dimethylbenzenesulfonamide (780 mg, 75%).

Workup

  1. washThe reaction was washed with 10 mL of 1N aqueous HCl and 10 mL of brine
  2. dry with materialOrganics were dried over Na2SO4
  3. customevaporated to dryness
  4. customCrude product was purified by chromatography on silica gel (eluting with 0-25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8c860f63217241d6911124aa5daffd4e
Source dataset
uspto-grants-2013_09
Patent number
US08524767B2

Reaction notes

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