Benzoyl chloride → 7-(bromomethyl)-5-fluoro-2,2-dimethylbenzofuran-3(2H)-one

HRID 445841Notes

Reaction equation

HRID 445841 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[C:7](=[O:12])[C:6]=2[CH:13]=1.[Br:15]N1C(=O)CCC1=O.C(Cl)(=O)C1C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:14][C:4]1[C:5]2[O:9][C:8]([CH3:10])([CH3:11])[C:7](=[O:12])[C:6]=2[CH:13]=[C:2]([F:1])[CH:3]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 585662995-fluoro-2,2,7-trimethylbenzofuran-3(2H)-one

Product 1

HCID 585667237-(bromomethyl)-5-fluoro-2,2-dimethylbenzofuran-3(2H)-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of provide 5-fluoro-2,2,7-trimethylbenzofuran-3(2H)-one (659) (100 mg, 0.515 mmol), N-Bromosuccinimide (100.8 mg, 0.567 mmol), benzoyl chloride (1.2 mg, 0.005 mmol) and carbon tetrachloride (2 mL) was heated at reflux overnight. Saturated sodium bicarbonate was added and extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated in vacuo. The crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (5%) to give 7-(bromomethyl)-5-fluoro-2,2-dimethylbenzofuran-3(2H)-one (660).

Workup

  1. temperatureat reflux overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude compound was purified by flash column chromatography on silica gel with hexanes and EtOAc (5%)

Sources & evidence

ORD record
ord-5a5b14efecee4ffaad26cabdcef2196a
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Reaction notes

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