Boron tribromide → 3-Chloro-4,5-dihydroxybenzaldehyde
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11]C)[C:9]=1[OH:10])[CH:5]=[O:6].B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[OH:10])[CH:5]=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 3-chloro-4-hydroxy-5-methoxy-benzaldehyde (10 g, 54 mmol) in dichloromethane (300 mL) was added BBr3 (26.7 g, 107 mmol) dropwise at −40° C. under N2. After addition, the mixture was stirred at this temperature for 5 h and then was poured into ice water. The precipitated solid was filtered and washed with petroleum ether. The filtrate was evaporated under reduced pressure to afford 3-chloro-4,5-dihydroxybenzaldehyde (9.8 g, 89%), which was directly used in the next step.
Workup
- additionAfter addition
- filtrationThe precipitated solid was filtered
- washwashed with petroleum ether
- customThe filtrate was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-e2bc1930aa774e02a90ff95ab6d98361
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08524767B2
Reaction notes
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