Water → 3-Chloro-5-hydroxybenzaldehyde

HRID 917292Notes

Reaction equation

HRID 917292 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10]C)[CH:9]=1)[CH:5]=[O:6].B(Br)(Br)Br.O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:10])[CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 219046333-Chloro-5-methoxybenzaldehyde

Product 1

HCID 219046483-Chloro-5-hydroxybenzaldehydeYield 25%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-chloro-5-methoxybenzaldehyde (22.8 g, 134 mmol; see step (i) above) in CH2Cl2 (250 mL) was cooled to 0° C. Boron tribromide (15.8 mL, 167 mmol) was added dropwise over 15 min. After stirring, the reaction-mixture for 2 h, H2O (50 mL) was added slowly. The solution was then extracted with Et2O (2×100 mL). The organic layers were combined, dried (Na2SO4), filtered and concentrated in vacuo. Flash chromatography on silica gel eluting with Hex:EtOAc (4:1) afforded the sub-title compound (5.2 g, 25%).

Workup

  1. extractionThe solution was then extracted with Et2O (2×100 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8bf2a4a29d9c489fb586c41bd0d186cc
Source dataset
uspto-grants-2007_09
Patent number
US07273858B2

Reaction notes

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