(Trifluoromethyl)trimethylsilane → 1-(4-Bromo-2-methylphenyl)-2,2,2-trifluoroethan-1-ol

HRID 1499261Notes

Reaction equation

HRID 1499261 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([CH3:10])[CH:3]=1.[Si]([C:15]([F:18])([F:17])[F:16])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.Cl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[C:15]([F:18])([F:17])[F:16])=[C:4]([CH3:10])[CH:3]=1

Participants

6

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 135551504-Bromo-2-methylbenzaldehyde

Product 1

HCID 867673941-(4-Bromo-2-methylphenyl)-2,2,2-trifluoroethan-1-ol

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-bromo-2-methylbenzaldehyde (1.5 g, 7.5 mmol) in THF (20 mL) was added TMSCF3 (2.2 g, 15.5 mmol) at 0° C. and then TBAF (1.1 mL, 1.0 M in THF). The mixture was stirred at RT for 1 h, then diluted with HCl (3.0 M, 10 mL), stirred at RT for 1 h and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. Purification by normal phase silica gel column provided 1-(4-bromo-2-methylphenyl)-2,2,2-trifluoroethanol as an off-white solid.

Workup

  1. stirringstirred at RT for 1 h
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification by normal phase silica gel column

Sources & evidence

ORD record
ord-2d7c2441c070452f9eab3b7f60dcc1fe
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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