Water → Methyl 3-bromo-5-(hydroxymethyl)benzoate

HRID 1845295Notes

Reaction equation

HRID 1845295 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7](OC)=[O:8].[BH4-].[Na+].O>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH2:7][OH:8])[CH:11]=1)[C:12]([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl esterHCID 4311764Sodium borohydride

Product 1

HCID 11356988Methyl 3-bromo-5-(hydroxymethyl)benzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of dimethyl 5-bromoisophthalate (5.4 g, 20 mmol) in methanol (300 mL) at 0° C. was slowly added sodium tetrahydroborate (10 g, 0.28 mol). The mixture was stirred at rt for 3 h, and then treated with water (300 mL). The volatiles were removed in vacuo and the aqueous phase was extracted with CH2Cl2 (100 mL×3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The resulting oil was purified by flash chromatography to afford the title compound.

Workup

  1. customat 0° C.
  2. customThe volatiles were removed in vacuo
  3. extractionthe aqueous phase was extracted with CH2Cl2 (100 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting oil was purified by flash chromatography

Sources & evidence

ORD record
ord-a1b7b49462ed48a7a879269b7aaeb92b
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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