Hydrochloric Acid → Methyl 3-bromo-5-(hydroxymethyl)benzoate

HRID 1862568Notes

Reaction equation

HRID 1862568 reaction equation
[Br:1][C:2]1(C(OC)=O)[CH:11]=[CH:10][CH:9]=[C:4]([C:5](OC)=[O:6])[CH2:3]1.[BH4-].[Na+].[CH3:18][OH:19].Cl.[O:21]1CCC[CH2:22]1>>[Br:1][C:2]1[CH:11]=[C:10]([CH:9]=[C:4]([CH2:5][OH:6])[CH:3]=1)[C:18]([O:21][CH3:22])=[O:19]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8028Tetrahydrofuran2×HCID 4311764Sodium borohydrideHCID 18620000HCID 18620000, compound

Product 1

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

Procedure

In 25 ml of tetrahydrofuran, was dissolved 10.00 g of dimethyl 3-bromoisophthalate. 1.66 g of sodium borohydride was added to the above solution and thereby a suspension was obtained. A mixed solution of 7.4 ml of methanol and 25 ml of tetrahydrofuran was slowly dropped into the resulting suspension. After completing the dropping, the reaction solution was refluxed for 30 minutes. A 1 M hydrochloric acid was added to the solution to quench the reaction. The resulting solution was extracted with ethyl acetate, and the organic layer was dried over magnesium sulfate. The solvent was removed under reduced pressure to afford 9.30 g of the title compound as a colorless oil quantitatively.

Workup

  1. customa suspension was obtained
  2. temperaturewas refluxed for 30 minutes
  3. customto quench
  4. customthe reaction
  5. extractionThe resulting solution was extracted with ethyl acetate
  6. dry with materialthe organic layer was dried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-682e4408f7cb4ceebbc142a72bf4d826
Source dataset
uspto-grants-2003_03
Patent number
US06538137B1

Reaction notes

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