Water → N-(3-bromo-phenyl)-2,2,2-trifluoro-N-methylacetamide

HRID 380031Notes

Reaction equation

HRID 380031 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].O.O1CCC[CH2:19]1>>[Br:1][C:2]1[CH:3]=[C:4]([N:8]([CH3:19])[C:9](=[O:14])[C:10]([F:11])([F:13])[F:12])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 3574082N-(3-bromophenyl)-2,2,2-trifluoroacetamide

Product 1

HCID 18367627N-(3-bromo-phenyl)-2,2,2-trifluoro-N-methylacetamide

Procedure

N-(3-Bromophenyl)-2,2,2-trifluoroacetamide (J. Chem. Soc., 1952, 4014) in tetrahydrofuran (3 ml) was added dropwise to sodium hydride (0.16 g) in tetrahydrofuran (5 ml). The reaction mixture was stirred for 30 minutes at room temperature. lodomethane (0.25 ml) was added dropwise to the reaction mixture and it was stirred overnight at room temperature. Water was added and the product extracted with ethyl acetate. The combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluting with iso-hexane: dichloromethane (1: 1) to give the sub-title compound as an oil (0.385 g).

Workup

  1. additionlodomethane (0.25 ml) was added dropwise to the reaction mixture and it
  2. stirringwas stirred overnight at room temperature
  3. extractionthe product extracted with ethyl acetate
  4. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography over silica gel eluting with iso-hexane: dichloromethane (1: 1)

Sources & evidence

ORD record
ord-64b1a9c5a99340808504b88c0a5ff75a
Source dataset
uspto-grants-2001_10
Patent number
US06300352B1

Reaction notes

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