Water → 3-(3-Bromo-4-fluorophenyl)-3-methylbutan-2-one

HRID 83880Notes

Reaction equation

HRID 83880 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([CH3:14])([CH3:13])[CH:10]([OH:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:9]([CH3:14])([CH3:13])[C:10](=[O:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 962WaterHCID 667406943-Bromo-4-fluoro-α,β,β-trimethylbenzeneethanolHCID 178418287HCID 178418287, compound

Product 1

HCID 667407993-(3-Bromo-4-fluorophenyl)-3-methylbutan-2-oneYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-(3-bromo-4-fluorophenyl)-3-methylbutan-2-ol (18 g, 69 mmol) in DCM (300 mL) at 0° C. was added PCC (29.7 g, 2 eq) portionwise. After stirring 24 h at room temperature, the reaction mixture was combined with water and extracted with DCM. The combined extracts were dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography (Hex/EtOAc=10:1) to give 3-(3-bromo-4-fluorophenyl)-3-methylbutan-2-one (13 g, 73%). 1H NMR (400 MHz, CDCl3) δ 7.47-7.45 (m, 1H), 7.17-7.14 (m, 1H), 7.09 (t, J=8.8 Hz, 1H), 1.98 (s, 3H), 1.45 (s, 6H).

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined extracts were dried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was purified by flash column chromatography (Hex/EtOAc=10:1)

Sources & evidence

ORD record
ord-07beb657f6724792b15a1259e1fa3fee
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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