Trifluoroacetic acid → 1-(4-Bromo-2-fluorophenyl)butan-1-one

HRID 537455Notes

Reaction equation

HRID 537455 reaction equation
FC(F)(F)C(O)=O.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:19])[CH2:16][CH2:17][CH3:18])=[C:11]([F:20])[CH:10]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:19])[CH2:16][CH2:17][CH3:18])=[C:11]([F:20])[CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 159087TriacetoxyperiodinaneHCID 63895095HCID 63895095, compound

Product 1

HCID 547590581-(4-Bromo-2-fluorophenyl)butan-1-oneYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (366 mL, 3.21 mmol) was added dropwise to a 0° C. solution of 1-(4-bromo-2-fluorophenyl)butan-ol (440 mg, 1.8 mmol) in dichloromethane (10 mL). Added Dess-Martin periodinane (1.21 g, 2.85 mmol) and let reaction warm to room temperature and stir for 2 hours. The reaction was quenched with 1 N aqueous sodium hydrosulfite (10 mL) and extracted with ethyl acetate (3×20 mL). The combined organics were dried over sodium sulfate, filtered, and concentrated. Purification by flash column chromatography gave 1-(4-bromo-2-fluorophenyl)butan-1-one (330 mg, 75%) as a colorless oil. 1H NMR (400 MHz, CDCl3, δ): 7.65-7.69 (m, 1H), 7.32-7.45 (m, 2H), 2.83-2.87 (m, 2H), 1.62-1.71 (m, 2H), 0.90 (m, 3H).

Workup

  1. customreaction
  2. customThe reaction was quenched with 1 N aqueous sodium hydrosulfite (10 mL)
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-434f2712bf064ae6860ea46f48653358
Source dataset
uspto-grants-2014_10
Patent number
US08859591B2

Reaction notes

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