Pyridine → N-(3-bromo-2-fluoro-phenyl)-2,5-difluoro-benzenesulfonamide

HRID 516635Notes

Reaction equation

HRID 516635 reaction equation
[Br:1][C:2]1[C:3]([F:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].N1C=CC=CC=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=1[S:24](Cl)(=[O:26])=[O:25]>C(Cl)Cl>[Br:1][C:2]1[C:3]([F:9])=[C:4]([NH:5][S:24]([C:18]2[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]=2[F:16])(=[O:26])=[O:25])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27369112,5-Difluorobenzenesulfonyl chlorideHCID 223418913-Bromo-2-fluoroaniline

Product 1

HCID 66729404N-(3-bromo-2-fluoro-phenyl)-2,5-difluoro-benzenesulfonamideYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Bromo-2-fluoroaniline (10 g, 52.63 mmol) was dissolved in DCM (100 mL) under nitrogen atmosphere. Dry pyridine was added (6 mL, 73.68 mmol, 1.4 eq), followed by 2,5-difluorobenzenesulfonyl chloride (7.08 mL, 52.63 mmol, 1 eq) and the mixture was stirred at r.t. for 2 h. It was then diluted with DCM and washed with aqueous 0.5 N HCl (3×80 mL) and brine. The organic layer was dried over Na2SO4 and evaporated to dryness. The solid was taken up with ethyl ether and stirred for 30 minutes. It was then filtered and dried at 40° C. under reduced pressure to give 17.8 g of N-(3-bromo-2-fluoro-phenyl)-2,5-difluoro-benzenesulfonamide as a pale yellow solid (92%). HPLC (254 nm): Rt: 6.28 min; 1H NMR (DMSO-d6) Shift: 10.86 (s, 1H), 7.50-7.73 (m, 4H), 7.23-7.31 (m, 1H), 7.12 (dt, J=1.3, 8.1 Hz, 1H).

Workup

  1. washwashed with aqueous 0.5 N HCl (3×80 mL) and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated to dryness
  4. stirringstirred for 30 minutes
  5. filtrationIt was then filtered
  6. customdried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-7b1330c97cbc4e55ad7642f37d8def3f
Source dataset
uspto-grants-2015_08
Patent number
US09114137B2

Reaction notes

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