Hydrochloric Acid → (3,5-Dibromophenyl)methanol

HRID 725030Notes

Reaction equation

HRID 725030 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([Br:12])[CH:11]=1)[CH:7]=[O:8].Cl>CO>[Br:3][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([Br:12])[CH:11]=1)[CH2:7][OH:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6220773,5-DibromobenzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 7009423(3,5-Dibromophenyl)methanolYield 94.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (0.75 g) was added portionwise to a stirred suspension of 3,5-dibromobenzaldehyde (10.46 g) in methanol (50 ml) at 0° C. The mixture was stirred at 0° C. for 30 minutes, allowed to warm to room temperature and then its pH was adjusted to 2 using concentrated hydrochloric acid. Evaporation under vacuum provided a residue which was partitioned between ethyl acetate and water. The organic phase was washed with water, dried(MgSO4), then evaporated under vacuum to furnish the title compound as a solid (10.0 g), m.p. 103°-104° C. Found: C, 31.98; H, 2.23. C7H6Br2O requires C, 31.61; H, 2.77%.

Workup

  1. temperatureto warm to room temperature
  2. customEvaporation under vacuum
  3. customprovided a residue which
  4. customwas partitioned between ethyl acetate and water
  5. washThe organic phase was washed with water, dried(MgSO4)
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-6a31763ce7e5436b85040d5a4941718f
Source dataset
uspto-grants-1998_01
Patent number
US05705523

Reaction notes

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