Hydrochloric Acid → 1-(4-Bromo-2-fluorophenyl)-2,2,2-trifluoroethanol

HRID 1400009Notes

Reaction equation

HRID 1400009 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=1.[F:11][C:12]([Si](C)(C)C)([F:14])[F:13].CCCC[N+](CCCC)(CCCC)CCCC.[F-].Cl>C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[C:12]([F:14])([F:13])[F:11])=[C:4]([F:10])[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride2×

Product 1

HCID 616446351-(4-Bromo-2-fluorophenyl)-2,2,2-trifluoroethanolYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 4-bromo-2-fluoro-benzaldehyde (8.12 g, 40.0 mmol) and (trifluoromethyl)trimethylsilane (7.50 mL, 48.0 mmol) in THF (40 mL) was cooled to 0° C. before treating with TBAF (1 M in THF, 0.6 mL) and warming to rt. After 3 h, an additional portion of TBAF (1 M in THF, 8.0 mL) was added. The resultant mixture was allowed to stir for 10 min before adding HCl (1 N aq., 40 mL) and extracting with Et2O (40 mL). The Et2O layer was dried (MgSO4) and concentrated to yield the title compound (10.7 g, 98%).

Workup

  1. temperaturewarming to rt
  2. extractionextracting with Et2O (40 mL)
  3. dry with materialThe Et2O layer was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b9623235aa6e4b86907322ddde276ceb
Source dataset
uspto-grants-2014_12
Patent number
US08906914B2

Reaction notes

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