HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1497641
Notes
Print preview

Reaction equation

HRID 1497641 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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), followed by 2,5-difluorobenzenesulfonyl chloride (7.08 mL, 52.63 mmol) 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 diethyl ether and stirred for 30 min. 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%).

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 min
  5. filtrationIt was then filtered
  6. customdried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-f1601dac8bd6494d8ba191f1adb94e5c
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09199979B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes