Formic Acid → N-(3-Bromo-phenyl)-N-methyl-formamide

HRID 2377434Notes

Reaction equation

HRID 2377434 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[NH:5][CH3:6].[CH:10]([OH:12])=O>O>[Br:1][C:2]1[CH:3]=[C:4]([N:5]([CH3:6])[CH:10]=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

4

Procedure

A solution of 3-bromo-N-methyl aniline (made as described by Lopez et al. in Tet. Lett., 1999, 40, 11, p2071-2074 incorporated herein by reference; 7.4 g, 39.5 mmol) in formic acid (20 mL) was refluxed for 3 h. The reaction mixture was then cooled to ambient temperature, diluted with water and extracted with diethyl ether. The organic phase was washed with saturated, aqueous sodium bicarbonate solution, water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title product as a dark brown oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe organic phase was washed with saturated, aqueous sodium bicarbonate solution, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-e1d55bb7cc294725aaf72822668f525c
Source dataset
uspto-grants-2008_12
Patent number
US07468391B2

Reaction notes

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