4-Hydroxybenzaldehyde → 3-Bromo-4-hydroxybenzaldehyde

HRID 2248024Notes

Reaction equation

HRID 2248024 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[Br:10]Br>C(Cl)(Cl)Cl>[Br:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[OH:1])[CH:6]=[O:7]

Participants

4

Reactant 2

HCID 1264-HydroxybenzaldehydeHCID 24408Bromine

Product 1

HCID 763083-Bromo-4-hydroxybenzaldehydeYield 45.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
40 °C

Procedure

To a solution of 4-hydroxybenzaldehyde (10.00 g, 82 mmol) in chloroform (170 mL) was added bromine (13.76 g, 86.1 mmol) dropwise as a solution in chloroform (80 mL). Upon completion of addition, the reaction was stirred for 30 mins. at room temperature then warmed to 40° C. for 1 hr. The reaction was diluted with aqu. sat'd NaHCO3 (250 mL) and the layers were separated. The aqueous was extracted with CH2Cl2 (2×250 mL). The organics were combined, dried with MgSO4 and concentrated to afford 7.49 g of 3-bromo-4-hydroxybenzaldehyde which contains 10% of 3,5-dibromo-4-hydroxybenzaldehyde.

Workup

  1. additionUpon completion of addition
  2. additionThe reaction was diluted with aqu
  3. customsat'd NaHCO3 (250 mL) and the layers were separated
  4. extractionThe aqueous was extracted with CH2Cl2 (2×250 mL)
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7636cee5ea82484d8b4baadf67d1af96
Source dataset
uspto-grants-1991_08
Patent number
US05037853

Reaction notes

Loading…