(Trifluoromethyl)trimethylsilane → 2-(6-Bromo-2-naphthyl)-1,1,1-trifluoropropan-2-ol

HRID 1094651Notes

Reaction equation

HRID 1094651 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12](=[O:14])[CH3:13])[CH:6]=[CH:5]2.C[Si]([C:19]([F:22])([F:21])[F:20])(C)C.CO.Cl>C([O-])(=O)C.[Li+].CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])([CH3:13])[C:19]([F:22])([F:21])[F:20])[CH:6]=[CH:5]2

Participants

6

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 124330821-(6-Bromonaphthalen-2-yl)ethanoneHCID 21893726Hydrochloride methanol

Product 1

HCID 666376052-(6-Bromo-2-naphthyl)-1,1,1-trifluoropropan-2-olYield 79.3%

Reagents, catalysts & solvents 2

HCID 3474584Lithium acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

To a DMF (25 ml) solution of 1-(6-bromo-2-naphthyl)ethanone (1230 mg, 4.94 mmol), trimethylsilyl trifluoromethane (1050 mg, 7.41 mmol) and lithium acetate (16.3 mg, 0.247 mmol) were added and the mixture was stirred for 12 hours at room temperature. Then, the reaction was quenched with ethyl acetate and water, then the organic layer was separated and dried over sodium sulfate. The solvent was evaporated to give the residue which was treated with methanol-hydrogen chloride to give the product (1.25 g, 63%) as colorless oil. 1H NMR (300 MHz, CDCl3) δ ppm 1.88 (3H, s), 7.57-7.60 (1H, m), 7.68-7.81 (3H, m), 8.02-8.05 (2H, m).

Workup

  1. customThen, the reaction was quenched with ethyl acetate and water
  2. customthe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated
  5. customto give the residue which

Sources & evidence

ORD record
ord-09b33e7513b64cddae994c4dd7595c3b
Source dataset
uspto-grants-2012_03
Patent number
US08134004B2

Reaction notes

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