Hydrochloric Acid → N-[3-bromo-5-(2,4-difluorophenoxy)phenyl]ethanesulfonamide

HRID 575791Notes

Reaction equation

HRID 575791 reaction equation
[CH2:1]([S:3](Cl)(=[O:5])=[O:4])[CH3:2].[Br:7][C:8]1[CH:9]=[C:10]([CH:12]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH:14]=1)[NH2:11].N1C=CC=CC=1.Cl>C(Cl)Cl>[Br:7][C:8]1[CH:9]=[C:10]([NH:11][S:3]([CH2:1][CH3:2])(=[O:5])=[O:4])[CH:12]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 11667Ethanesulfonyl chlorideHCID 1180219103-Bromo-5-(2,4-difluorophenoxy)aniline

Product 1

HCID 118021931N-[3-bromo-5-(2,4-difluorophenoxy)phenyl]ethanesulfonamideYield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethylsulfonyl chloride (15 uL, 0.16 mmol) was added dropwise to a stirred solution of 3-bromo-5-(2,4-difluorophenoxy)aniline (48 mg, 0.16 mmol) and pyridine (40 uL, 0.48 mmol) in DCM (320 uL) at 0° C. under nitrogen. After the mixture was allowed to warm to rt and stir for 12 h, it was treated with 1N HCl (1 mL) and extracted with DCM (3×5 mL); the combined organic extracts were washed with saturated bicarbonate solution (aq), dried over sodium sulfate, filtered and concentrated in vacuo. The crude solid was purified by silica gel column chromatography using a gradient of EtOAc (5 to 60%) in hexanes to afford the title compound (60 mg, 95%) as a tan solid. LCMS (M+H)+=393.

Workup

  1. extractionextracted with DCM (3×5 mL)
  2. washthe combined organic extracts were washed with saturated bicarbonate solution (aq)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude solid was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-08e03e7a9a3d4875baed0b35c8a6f0cd
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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