Sulfuric Acid → 1-(4-Fluoro-3-(trifluoromethyl)phenyl)-2-methylpropan-1-ol

HRID 1295595Notes

Reaction equation

HRID 1295595 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:12])=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[Mg].[CH:14](=[O:18])[CH:15]([CH3:17])[CH3:16].S(=O)(=O)(O)O>C(OCC)C>[F:12][C:5]1[CH:4]=[CH:3][C:2]([CH:14]([OH:18])[CH:15]([CH3:17])[CH3:16])=[CH:7][C:6]=1[C:8]([F:11])([F:10])[F:9]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 6561IsobutyraldehydeHCID 27363255-Bromo-2-fluorobenzotrifluorideHCID 5462224Magnesium

Product 1

HCID 231059461-(4-Fluoro-3-(trifluoromethyl)phenyl)-2-methylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A Grignard is prepared from 10 g (40 mmol) 5-bromo-2-fluorobenzotrifluoride, dissolved in 50 mL diethyl ether, and 0.97 g (40 mmol) magnesium. Then a solution of 3.63 mL (40 mmol) isobutyraldehyde and 30 mL diethyl ether is added dropwise at ambient temperature and the mixture is left overnight with stirring. The reaction mixture is poured onto ice water, combined with 30 mL 20% sulphuric acid and extracted with diethyl ether. The combined organic phases are washed successively with sodium hydrogen carbonate solution, water and sodium chloride solution, dried with sodium sulphate and evaporated down. The chromatographic purification of the residue yields the target compound in the form of a brown oil.

Workup

  1. additionThe reaction mixture is poured onto ice water
  2. extractionextracted with diethyl ether
  3. washThe combined organic phases are washed successively with sodium hydrogen carbonate solution, water and sodium chloride solution
  4. dry with materialdried with sodium sulphate
  5. customevaporated down
  6. customThe chromatographic purification of the residue
  7. customyields the target compound in the form of a brown oil

Sources & evidence

ORD record
ord-d068c1a9b0c74d499b7413f97274e6be
Source dataset
uspto-grants-2007_07
Patent number
US07244728B2

Reaction notes

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