Water → 2-(1,1-Dimethyl-3-hydroxy-3-trifluoromethyl-5-hexynyl)-4-fluorotoluene

HRID 2387299Notes

Reaction equation

HRID 2387299 reaction equation
[Al].[CH2:2](Br)[C:3]#[CH:4].[F:6][C:7]([F:23])([F:22])[C:8](=[O:21])[CH2:9][C:10]([C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[CH3:20])([CH3:12])[CH3:11].O>C1COCC1.C(OCC)C.C(OCC)(=O)C>[F:19][C:17]1[CH:16]=[CH:15][C:14]([CH3:20])=[C:13]([C:10]([CH3:12])([CH3:11])[CH2:9][C:8]([C:7]([F:6])([F:22])[F:23])([OH:21])[CH2:4][C:3]#[CH:2])[CH:18]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 5359268AluminumHCID 207961201,1,1-Trifluoro-4-(5-fluoro-2-methylphenyl)-4-methylpentan-2-one

Product 1

HCID 469390162-(1,1-Dimethyl-3-hydroxy-3-trifluoromethyl-5-hexynyl)-4-fluorotolueneYield 100.4%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Aluminum foil (324 mg, 12 mmol) and mercuric chloride (5.0 g, 0.02 mmol) were added to THF (6 mL) and vigorously stirred for 1 hour. Propargyl bromide (1.34 mL, 80% in toluene, 12 mmol) in 6 mL of THF was added slowly and the mixture heated up. After completion of the addition, the mixture was stirred for 2 hours at 40° C. and for 3 hours at room temperature. Half of the generated suspension was added via syringe to a solution of 1,1,1-trifluoro-4-(5-fluoro-2-methylphenyl)-4-methylpentan-2-one (500 mg, 1.91 mmol) in 20 mL of diethyl ether at −78° C. The reaction mixture was warmed up slowly to room temperature overnight. Water (20 mL) and ethyl acetate (20 mL) were added slowly. The organic phase was separated and the aqueous layer was extracted with two 10 mL portions of ethyl acetate. The combined organic phases were dried over magnesium sulfate. The solvent was removed to give 6-(5-fluoro-2-methylphenyl)-6-methyl-4-trifluoromethylhept-1-yn-4-ol (580 mg, 100%) as a colorless oil.

Workup

  1. temperaturethe mixture heated up
  2. additionAfter completion of the addition
  3. stirringthe mixture was stirred for 2 hours at 40° C. and for 3 hours at room temperature
  4. customThe organic phase was separated
  5. extractionthe aqueous layer was extracted with two 10 mL portions of ethyl acetate
  6. dry with materialThe combined organic phases were dried over magnesium sulfate
  7. customThe solvent was removed

Sources & evidence

ORD record
ord-2c91d7e543f6495dbcae7a74d1017156
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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