Diethyl Ether → 2-(2-Bromophenyl)ethan-1-ol
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9](O)=[O:10].[BH4-].[Na+].B(F)(F)F.CCOCC>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][OH:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of (2-bromophenyl)acetic acid (100 g, 0.46 mmol) in dry THF (2 L) was added NaBH4 (29 g, 0.77 mol) in portions. The contents were cooled to 0° C., and BF3. Et2O (123 mL, 0.77 mol) was added drop wise over 1 h. The mixture was allowed to warm to 25° C. and stirred for 16 h. The reaction was cooled to 0° C. and cautiously quenched with aqueous sodium hydroxide. The contents were stirred for 3 h, and then extracted with EtOAc. The organic layer was dried and concentrated to give 2-(2-bromophenyl)ethanol.
Workup
- temperatureto warm to 25° C.
- temperatureThe reaction was cooled to 0° C.
- customcautiously quenched with aqueous sodium hydroxide
- stirringThe contents were stirred for 3 h
- extractionextracted with EtOAc
- customThe organic layer was dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-e707e7f224dd4fdda7b88dbdddb678a4
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08673920B2
Reaction notes
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