N-bromobutanimide → 3'-Bromo-4'-hydroxy-5'-(trifluoromethyl)acetophenone

HRID 249723Notes

Reaction equation

HRID 249723 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1)=[O:3].[Br:15]N1C(=O)CCC1=O>C(#N)C>[Br:15][C:8]1[CH:9]=[C:4]([C:2](=[O:3])[CH3:1])[CH:5]=[C:6]([C:11]([F:12])([F:13])[F:14])[C:7]=1[OH:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 27751094'-Hydroxy-3'-(trifluoromethyl)acetophenone

Product 1

HCID 580857003'-Bromo-4'-hydroxy-5'-(trifluoromethyl)acetophenone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Hydroxy-3-(trifluoromethyl)acetophenone (4 g) was initially introduced in acetonitrile (150 ml) and N-bromosuccinimide (4.5 g, dissolved in 100 ml acetonitrile) was added dropwise at −10° C. After addition was complete, the cooling bath was removed and the mixture was stirred for 5 h. After standing overnight, the volume of solvent was reduced to a quarter and the residue was treated with n-heptane/water. After separating off the organic phase, this was washed once with 5% strength sodium thiosulfate solution and once with water. The precipitate formed in the course of this (6.9 g) was filtered off with suction and directly reacted further in the next stage.

Workup

  1. additionAfter addition
  2. customthe cooling bath was removed
  3. waitAfter standing overnight
  4. additionthe residue was treated with n-heptane/water
  5. customAfter separating off the organic phase
  6. washthis was washed once with 5% strength sodium thiosulfate solution and once with water
  7. customThe precipitate formed in the course of this (6.9 g)
  8. filtrationwas filtered off with suction
  9. customdirectly reacted further in the next stage

Sources & evidence

ORD record
ord-0e04d23518e74dbda8e65ced2c99f3ff
Source dataset
uspto-grants-2011_01
Patent number
US07863269B2

Reaction notes

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