2-Amino-2-(2-bromophenyl)acetic acid → HCID 14853184, compound
Reaction equation
[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Br:12])[C:3](O)=[O:4].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[Br:12])[CH2:3][OH:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 2-amino-2-(2-bromophenyl)acetic acid (4.89 g, 21.3 mmol) in THF (50 mL) was added dropwise a solution of LiAlH4 in THF (1.0 M, 42.5 mL, 42.5 mmol) at 0° C. under N2. The reaction was allowed to warm to ambient temperature and stirred for 4 hours. The reaction mixture was cooled to 0° C. and carefully quenched by dropwise addition of water (1.7 mL) followed by 15% NaOH solution (1.7 mL) and water (5.1 mL). The mixture was stirred at ambient temperature for 15 minutes and filtered through Celite. The filtrate was concentrated to give crude 2-amino-2-(2-bromophenyl)ethanol, which was used in the next step without further purification.
Workup
- temperatureThe reaction mixture was cooled to 0° C.
- customcarefully quenched by dropwise addition of water (1.7 mL)
- stirringThe mixture was stirred at ambient temperature for 15 minutes
- filtrationfiltered through Celite
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-8afb829c4c7343829573f8da7c8b5c4b
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865726B2
Reaction notes
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