Water → 4-(Bromomethyl)-3-(trifluoromethyl)benzoic acid

HRID 1478135Notes

Reaction equation

HRID 1478135 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[C:6]([C:11]([F:14])([F:13])[F:12])[CH:5]=1.C1C(=O)N([Br:23])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:15])=[CH:5][C:6]=1[C:11]([F:14])([F:13])[F:12]

Participants

6

Reactant 4

HCID 962WaterHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 11952921Methyl 4-methyl-3-(trifluoromethyl)benzoate

Product 1

HCID 231458934-(Bromomethyl)-3-(trifluoromethyl)benzoic acidYield 140.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4-Methyl-3-(trifluoromethyl)benzoic acid methyl ester (3.73 g, 18.3 mmol) in CCl4 (40 mL) with NBS (3.9 g, 22 mmol) and benzoylperoxide with 25% of water (0.55 g, 1.7 mmol) were stirred and heated to reflux for 6 h. Solvent was evaporated, a water solution of K2CO3 was added and product is extracted with EtOAc to obtain a pale yellow solid (7.64 g, 25.7 mmol). Yield=140% (crude).

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 h
  3. customSolvent was evaporated
  4. additiona water solution of K2CO3 was added
  5. extractionproduct is extracted with EtOAc

Sources & evidence

ORD record
ord-182901455e984b198d16ff2540ad88ef
Source dataset
uspto-grants-2016_08
Patent number
US09403823B2

Reaction notes

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