Sodium borohydride → Methyl 3-bromo-5-(hydroxymethyl)-4-methylbenzoate

HRID 337658Notes

Reaction equation

HRID 337658 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH:13]=[O:14])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:13][OH:14])[C:11]=1[CH3:12])[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86651684Methyl 3-bromo-5-formyl-4-methylbenzoate

Product 1

HCID 66896191Methyl 3-bromo-5-(hydroxymethyl)-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a methanol (0.1 M) solution of methyl 3-bromo-5-formyl-4-methylbenzoate (1 eq.) from the previous step was added sodium borohydride (4 eq.) portionwise. The resulting mixture was stirred at RT for 3 h. The reaction was subsequently quenched with cold 10% aq. HCl and extracted with ether. The combined organic extracts were then washed with water and brine, dried over Na2SO4 and filtered. Concentration of the filtrate in vacuo afforded the title compound as a white solid.

Workup

  1. customThe reaction was subsequently quenched with cold 10% aq. HCl
  2. extractionextracted with ether
  3. washThe combined organic extracts were then washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-fafbeae335f44fd68172e70daf5e7c8a
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

Loading…