Trifluoroacetic acid → 4-Bromo-2-fluoro-1-(1-methylethyl)benzene

HRID 1453035Notes

Reaction equation

HRID 1453035 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](O)([CH3:10])[CH3:9])=[C:4]([F:12])[CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:9])[CH3:10])=[C:4]([F:12])[CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 587621954-Bromo-2-fluoro-alpha,alpha-dimethylbenzenemethanol

Product 1

HCID 210510924-Bromo-2-fluoro-1-(1-methylethyl)benzeneYield 80.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-bromo-2-fluorophenyl)propan-2-ol (7.6 g, 32.8 mmol) dissolved in anhydrous CH2Cl2 (300 mL) at 25° C. was added triethylsilane (7.8 mL, 49.1 mmol), followed by trifluoroacetic acid (25 mL, 328 mmol). The resulting solution was stirred at that temperature for 45 min. The solvent was removed in vacuo and the residue was purified by flash column chromatography (0-10% EtOAc in hexanes) to give the desired product (5.7 g, 80% yield). 1H NMR (CDCl3, 400 MHz) δ: 1.23 (d, J=6.82 Hz, 3H), 3.15-3.22 (m, 1H), 7.11 (t, J=8.08 Hz, 1H), 7.17 (dd, J=9.85, 1.77 Hz, 1H), 7.22 (d, J=8.34 Hz, 1H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash column chromatography (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5dcac8f45c9b47088064164ba947ae88
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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