3,5-Dibromobenzaldehyde → (3,5-Dibromophenyl)methanol

HRID 2428074Notes

Reaction equation

HRID 2428074 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:10])[CH:9]=1)[CH:5]=[O:6].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:10])[CH:9]=1)[CH2:5][OH:6]

Participants

4

Conditions

Temperature
0 °C

Procedure

3,5-Dibromobenzaldehyde (1.7 g, 6.3 mmol) was dissolved in methanol (100 mL) and sodium borohydride (0.250 g, 6.3 mmol) was added at 0° C. The reaction mixture was stirred for 0.5 h at 0° C. and then at 20° C. for another 0.5 h. The reaction mixture was concentrated in vacuo, diluted with brine (250 mL), acidified with hydrochloric acid and extracted with dichloromethane (3×50 mL). Evaporation of the organic solution gave 3,5-dibromo-benzyl alcohol as a white crystalline compound.

Workup

  1. waitat 20° C. for another 0.5 h
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with brine (250 mL)
  4. extractionextracted with dichloromethane (3×50 mL)
  5. customEvaporation of the organic solution

Sources & evidence

ORD record
ord-4cb25c0e0f3a4d0ca4148708a40f6b8e
Source dataset
uspto-grants-2011_06
Patent number
US07968723B2

Reaction notes

Loading…