Dichloromethane → 2-Chloro-3,4-dihydroxybenzaldehyde

HRID 1283891Notes

Reaction equation

HRID 1283891 reaction equation
[Cl:1][C:2]1[C:9]([OH:10])=[C:8]([O:11]C)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(Cl)Cl.B(Br)(Br)Br>CO>[Cl:1][C:2]1[C:9]([OH:10])=[C:8]([OH:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 603956Chloroisovaniline

Product 1

HCID 5988142-Chloro-3,4-dihydroxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 25 g. (0.134 m.) of 2-chloroisovanillin in 80 ml. of methylene chloride at 0°C. is added dropwise 19 ml. (0.2 m.) of boron tribromide and the mixture is stirred at 25°C. for 3 hours. Methanol (100 ml.) is added and the solution is concentrated to give 2-chloroprotocatechualdehyde, m.p. 193°-195°C.

Workup

  1. concentrationthe solution is concentrated

Sources & evidence

ORD record
ord-bf9933328a3f48abadf48c4b2bc089d5
Source dataset
uspto-grants-1976_08
Patent number
US03976695

Reaction notes

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