Boron tribromide → 2-Chloro-4,5-dihydroxybenzaldehyde

HRID 1283896Notes

Reaction equation

[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([O:10]C)=[C:4]([O:12]C)[CH:3]=1.B(Br)(Br)Br>>[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([OH:10])=[C:4]([OH:12])[CH:3]=1

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 2793512-Chloro-4,5-dimethoxybenzaldehyde

Product 1

HCID 5988132-Chloro-4,5-dihydroxybenzaldehyde

Procedure

6-Chloroveratraldehyde is treated with boron tribromide as described in Example 4 to give 6-chloroprotocatechualdehyde as a white solid, m.p. 217°-218°C. which is dibenzylated to give 6-chloro-3,4-dibenzyloxybenzaldehyde, m.p. 100°-102°C.

Sources & evidence

ORD record: ord-bc947144bc5d436986e1bb4c587f5d60
Source dataset: uspto-grants-1976_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03976695

Reaction notes

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