Hydrochloric Acid → 2-(6-Bromo-2-naphthyl)-1,1,1-trifluoropropan-2-ol

HRID 2425570Notes

Reaction equation

HRID 2425570 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.[F:15][C:16]([Si](C)(C)C)([F:18])[F:17].C([O-])(=O)C.[Li+].Cl>CO.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:16]([F:18])([F:17])[F:15])[CH:6]=[CH:5]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 552549(Trifluoromethyl)trimethylsilaneHCID 3474584Lithium acetateHCID 124330821-(6-Bromonaphthalen-2-yl)ethanone

Product 1

HCID 666376052-(6-Bromo-2-naphthyl)-1,1,1-trifluoropropan-2-olYield 83%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a DMF (25 ml) solution of 1-(6-bromo-2-naphthyl)ethanone (2.5 g, 10.0 mmol, Tetrahedron Letters (2001), 42(2), 265-266), trifluoromethyltrimethylsilane (2.14 g, 15.1 mmol) and lithium acetate (33.1 mg, 0.5 mmol) were added and the mixture was stirred for 12 hrs at room temperature. Then, the reaction was partitioned with sodium acetate aqueous solution and ethylacetate. The organic layer was dried over sodium sulfate and filtered. Then, evaporation gave the crude residue which was treated with hydrogen chloride and methanol with stirring for 5 hrs. Then, evaporation gave the crude residue which was purified through silica gel column chromatography, eluting with hexane:ethyl acetate (5:1), to give the title compound as colorless oil in 83% yield. 1H NMR (300 MHz, CDCl3) 2.50 (1H, s), 7.58 (1H, d, J=8.8 Hz), 771-7.81 (3H, m), 8.04 (2H, d, J=8.9 Hz).

Workup

  1. customThen, the reaction was partitioned with sodium acetate aqueous solution and ethylacetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customThen, evaporation
  5. customgave the crude residue which
  6. stirringwith stirring for 5 hrs
  7. customThen, evaporation
  8. customgave the crude residue which
  9. customwas purified through silica gel column chromatography
  10. washeluting with hexane:ethyl acetate (5:1)

Sources & evidence

ORD record
ord-fec31cc89f8d477d980e448dc4508d99
Source dataset
uspto-grants-2011_06
Patent number
US07964732B2

Reaction notes

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