Water → HCID 57721734, compound

HRID 1986158Notes

Reaction equation

HRID 1986158 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH2:7][OH:8].CC(C)([O-])C.[K+].F[C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[N+:28]([O-:30])=[O:29].O>C1COCC1>[F:27][C:25]1[CH:26]=[CH:21][C:22]([N+:28]([O-:30])=[O:29])=[C:23]([O:8][CH2:7][CH2:6][C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([C:2]([F:12])([F:13])[F:1])[CH:4]=2)[CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 679672,4-DifluoronitrobenzeneHCID 959263-(Trifluoromethyl)phenethylic alcoholHCID 23665647Potassium tert-butoxide

Product 1

HCID 57721734HCID 57721734, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolved 3-(trifluoromethyl)phenethyl alcohol (657 mg, 3.46 mmol) in THF (5 mL). After cooling to 0° C., potassium tert-butoxide (1M THF, 4.08 mmol, 4.08 mL) was added and the mixture was warmed to ambient temperature and stirred for 30 min. The reaction mixture was cooled to −78° C., and 2,4-difluoronitrobenzene (500 mg, 3.14 mmol) was added. The reaction mixture was allowed to slowly warm to ambient temperature. The mixture was poured into H2O and extracted with EtOAc (2×). The combined organics were washed with brine and dried over Na2SO4. The title compound was purified by crystallization from a EtOAc:Hexane mixture.

Workup

  1. temperaturethe mixture was warmed to ambient temperature
  2. temperatureThe reaction mixture was cooled to −78° C.
  3. temperatureto slowly warm to ambient temperature
  4. extractionextracted with EtOAc (2×)
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. customThe title compound was purified by crystallization from a EtOAc

Sources & evidence

ORD record
ord-fd8bf3a2074f4b6a982126e9d37e92a6
Source dataset
uspto-grants-2009_06
Patent number
US07547804B2

Reaction notes

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