Ethanol → (2-Amino-4-bromophenyl)methanol
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1.[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:10][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[CH2:8][OH:9]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
A mixture of (4-bromo-2-nitro-phenyl)-methanol (1.85 g, 7.97 mmol), iron powder (2.23 g, 39.9 mmol), ammonium chloride (213 mg, 3.99 mmol), ethanol (20 mL), and water (10 mL) was heated at 75° C. for 1 h, then after cooling filtered through a pad of diatomaceous earth. The filtrate was evaporated and the residue partitioned between ethyl acetate and water, the organic layer was washed with brine, dried (MgSO4), and evaporated to produce (2-amino-4-bromo-phenyl)-methanol (1.53 g, 90%). Off-white solid, MS (EI)=201.0 (M+).
Workup
- temperatureafter cooling
- filtrationfiltered through a pad of diatomaceous earth
- customThe filtrate was evaporated
- customthe residue partitioned between ethyl acetate and water
- washthe organic layer was washed with brine
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-750b8360f5894fb8a77b7e6101fc8346
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879845B2
Reaction notes
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