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

HRID 532394Notes

Reaction equation

HRID 532394 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[Br:15]N1C(=O)CCC1=O>C(#N)C>[Br:15][C:7]1[CH:6]=[C:5]([C:8](=[O:10])[CH3:9])[CH:4]=[C:3]([C:11]([F:12])([F:13])[F:14])[C:2]=1[OH:1]

Participants

4

Reactant 2

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

Product 1

HCID 580857003'-Bromo-4'-hydroxy-5'-(trifluoromethyl)acetophenoneYield 99.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
-10 °C

Procedure

1-(4-Hydroxy-3-trifluoromethylphenyl)ethanone (5 g) was initially charged in acetonitrile (150 ml) at RT while stirring, and cooled to −10° C. At this temperature, N-bromosuccinimide (4.5 g, dissolved in 100 ml of acetonitrile) was added dropwise. Then the cooling bath was removed and the mixture was stirred for a further 5 h. After standing overnight, ¾ of the solvent was drawn off and the residue was admixed with n-heptane/water. The organic phase was removed and washed once with 5% sodium thiosulfate solution and once with water. The precipitate formed was filtered off with suction, washed and dried. 6.9 g of the title compound were obtained in sufficient purity. LC-MS rt: 1.35 min [M+H]+: 283.0 (met. a)

Workup

  1. customThen the cooling bath was removed
  2. stirringthe mixture was stirred for a further 5 h
  3. customThe organic phase was removed
  4. washwashed once with 5% sodium thiosulfate solution and once with water
  5. customThe precipitate formed
  6. filtrationwas filtered off with suction
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-10914e120f7544eebfabf619841b6a36
Source dataset
uspto-grants-2014_10
Patent number
US08853206B2

Reaction notes

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