Aluminium lithium hydride → (4-(Fluoromethoxy)-3-(trifluoromethyl)phenyl)methanol

HRID 1964128Notes

Reaction equation

HRID 1964128 reaction equation
[F:1][CH2:2][O:3][C:4]1[CH:13]=[CH:12][C:7]([C:8](OC)=[O:9])=[CH:6][C:5]=1[C:14]([F:17])([F:16])[F:15].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(Cl)Cl>[F:1][CH2:2][O:3][C:4]1[CH:13]=[CH:12][C:7]([CH2:8][OH:9])=[CH:6][C:5]=1[C:14]([F:15])([F:16])[F:17]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67249754Methyl 4-(fluoromethoxy)-3-(trifluoromethyl)benzoate

Product 1

HCID 67250584(4-(Fluoromethoxy)-3-(trifluoromethyl)phenyl)methanolYield 84.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (−78° C.) solution of methyl 4-(fluoromethoxy)-3-(trifluoromethyl)benzoate (2.44 g, 9.68 mmol) in DCM under nitrogen was added 2.0 M LAH (4.84 mL, 9.68 mmol) by syringed. The reaction was stirred for 15 min. The reaction was quenched with water (0.484 mL) and 10% NaOH (0.968 mL). The mixture was filtered and concentrated to give the title compound as an oil (1.84 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 4.52 (d, J=5.68 Hz, 2H), 5.32 (t, J=5.75 Hz, 1H), 5.85-6.08 (d, J=53.44 Hz, 2H), 7.39 (d, J=8.46 Hz, 1H), 7.56-7.69 (m, 2H); 19F NMR (376 MHz, DMSO-d6) δ ppm −151.41 (s, 1F), −60.26 (s, 3F).

Workup

  1. customThe reaction was quenched with water (0.484 mL) and 10% NaOH (0.968 mL)
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2b6b659d199d46898a674986a17c9ee0
Source dataset
uspto-grants-2013_04
Patent number
US08415484B2

Reaction notes

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