Ammonium Chloride → 2-Methyl-1-(3-trifluoromethyl-phenyl)-propan-2-ol

HRID 1295599

Reaction equation

HRID 1295599 reaction equation
[CH3:1][Mg]Br.[F:4][C:5]([F:17])([F:16])[C:6]1[CH:7]=[C:8]([CH2:12][C:13](=[O:15])[CH3:14])[CH:9]=[CH:10][CH:11]=1.[Cl-].[NH4+]>C(OCC)C.C1COCC1>[CH3:14][C:13]([OH:15])([CH3:1])[CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([C:5]([F:16])([F:17])[F:4])[CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 891011-(alpha,alpha,alpha-Trifluoro-m-tolyl)acetoneHCID 178418573HCID 178418573, compound

Product 1

HCID 149749932-Methyl-1-(3-trifluoromethyl-phenyl)-propan-2-ol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

90 mL of a 3 molar solution of methylmagnesium bromide in diethyl ether are diluted with 300 mL THF and cooled to −50° C. At this temperature 20 g 1-(3-trifluoromethyl-phenyl)-propan-2-one, dissolved in 100 mL THF, are added dropwise. After the addition has ended the reaction mixture is stirred overnight while heating to ambient temperature. It is combined with ammonium chloride solution and extracted with diethyl ether. The combined organic phases are washed with sodium chloride solution, dried with sodium sulphate and evaporated down. The residue remaining is purified by chromatography.

Workup

  1. additionare added dropwise
  2. additionAfter the addition
  3. temperaturewhile heating to ambient temperature
  4. extractionextracted with diethyl ether
  5. washThe combined organic phases are washed with sodium chloride solution
  6. dry with materialdried with sodium sulphate
  7. customevaporated down
  8. customThe residue remaining is purified by chromatography

Sources & evidence

ORD record
ord-2a031326e45f4a968da9f97965d6ff33
Source dataset
uspto-grants-2007_07
Patent number
US07244728B2

Linked notes

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