Water → HCID 86752684, compound

HRID 962432Notes

Reaction equation

HRID 962432 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([NH:12][C:13](=[O:22])[C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=1[F:21])[CH2:9][CH2:10][OH:11].C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32].O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([NH:12][C:13](=[O:22])[C:14]1[C:19]([F:20])=[CH:18][CH:17]=[CH:16][C:15]=1[F:21])[CH2:9][CH2:10][O:11][S:31]([CH3:30])(=[O:33])=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19085384N-[1-(2-Bromophenyl)-3-hydroxypropyl]-2,6-difluorobenzamide

Product 1

HCID 86752684HCID 86752684, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 15.0 g of N-[1-(2-bromophenyl)-3-hydroxypropyl]-2,6-difluorobenzamide, 4.5 g of triethylamine in 150 ml of dichloromethane at room temperature, was added dropwise 5.1 g of methylsulfonyl chloride and stirring continued for an additional 30 minutes. The reaction mixture was poured into iced water and extracted with ethyl acetate. The ethyl acetate solution was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to afford 18.0 g of N-[1-(2-bromophenyl)-3-(methylsulfonyloxy)propyl]-2, 6-difluorobenzamide.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate solution was washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b9a76359eb504d8eb46fb9796f9f1748
Source dataset
uspto-grants-1998_06
Patent number
US05760033

Reaction notes

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