Hydrochloric Acid → 5-Bromo-2-methoxybenzoic acid

HRID 558321Notes

Reaction equation

HRID 558321 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[K+].Cl>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13297188Methyl 5-bromo-2-methoxybenzoate

Product 1

HCID 8817395-Bromo-2-methoxybenzoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 5-bromo-2-methoxybenzoate (14.7 g) obtained in step A was dissolved in 100 mL of methanol. To the solution, 40 mL of a 20% aqueous solution of potassium hydroxide was added, and the mixture was stirred for 2 hours at 80° C. The reaction solution was cooled to 0° C., and then adjusted to pH of about 3 with the use of 11 mL of concentrated hydrochloric acid. The precipitate was separated by filtration, washed with water, and then dried over diphosphorus pentoxide under reduced pressure to obtain 10.9 g (85%) of 5-bromo-2-methoxybenzoic acid.

Workup

  1. temperatureThe reaction solution was cooled to 0° C.
  2. customThe precipitate was separated by filtration
  3. washwashed with water
  4. dry with materialdried over diphosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-b5e37bec61e74f3382a6c1f9448adb30
Source dataset
uspto-grants-2011_11
Patent number
US08063046B2

Reaction notes

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