Aluminium lithium hydride → [4-Bromo-3-(2,2,2-trifluoroethyl)phenyl]methanol
Reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][C:3]=1[CH2:12][C:13]([F:16])([F:15])[F:14].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[CH:4][C:3]=1[CH2:12][C:13]([F:14])([F:15])[F:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Into a 100-mL round-bottom flask, was placed a solution of methyl 4-bromo-3-(2,2,2-trifluoroethyl)benzoate (900 mg, 3.03 mmol, 1.00 equiv) in tetrahydrofuran (30 mL). This was followed by the addition of LAH (231 mg, 6.09 mmol, 2.00 equiv), in portions at 0° C. The resulting solution was stirred for 2 h at 0° C. The reaction was then quenched by the addition of 5 g of sodium sulfate. 10H2O. The solids were filtered out. The resulting mixture was concentrated under vacuum. This resulted in 800 mg (98%) of [4-bromo-3-(2,2,2-trifluoroethyl)phenyl]methanol as yellow oil.
Workup
- customInto a 100-mL round-bottom flask, was placed
- customThe reaction was then quenched by the addition of 5 g of sodium sulfate
- filtrationThe solids were filtered out
- concentrationThe resulting mixture was concentrated under vacuum
- customThis resulted in 800 mg (98%) of [4-bromo-3-(2,2,2-trifluoroethyl)phenyl]methanol as yellow oil
Sources & evidence
- ORD record
- ord-92823b5179524bdfbcd271f459addf97
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447084B2
Reaction notes
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