1,2-Dimethyl 4-bromobenzene-1,2-dicarboxylate → (5-Bromo-2-(hydroxymethyl)phenyl)methanol
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12](OC)=[O:13])[C:5](=[CH:10][CH:11]=1)[C:6](OC)=[O:7].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[C:4]([CH2:12][OH:13])[CH:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
The compound of example 668 (2 g, 7.326 mmol) was taken in dry THF and was added to a slurry of LiAlH4 (1.67 g, 43.95 mmol) in THF cooled to 0° C. The reaction mixture was stirred at room temperature for 1 h. The reaction mixture was quenched with aqueous NaOH solution followed by extraction with ethyl acetate. The solvent was removed by distillation to afford the title compound.
Workup
- customThe reaction mixture was quenched with aqueous NaOH solution
- extractionfollowed by extraction with ethyl acetate
- customThe solvent was removed by distillation
Sources & evidence
- ORD record
- ord-d8ab5a7b82304f878bd6cd3318476370
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08748426B2
Reaction notes
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