Sodium Hydroxide → 3-Bromo-4-cyclopropylbenzoic acid

HRID 1487855Notes

Reaction equation

HRID 1487855 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH:12]1[CH2:14][CH2:13]1)[C:5]([O:7]C)=[O:6].[OH-].[Na+]>CO.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH:12]1[CH2:13][CH2:14]1)[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 44828964Methyl 3-bromo-4-cyclopropylbenzoate2×

Product 1

HCID 448285263-Bromo-4-cyclopropylbenzoic acidYield 63.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Into a 50-mL round-bottom flask, was placed a solution of methyl 3-bromo-4-cyclopropylbenzoate (compound 10.2, 500 mg, 1.96 mmol) in methanol (10 mL) and a solution of sodium hydroxide (500 mg, 12.5 mmol) in water (5 mL). The resulting solution was stirred overnight at 50° C., then the volatiles were removed under reduced pressure. The pH of the residual solution was adjusted to 6-7 with aqueous HCl (6 M). The resulting solids were collected by filtration to yield 0.3 g (63%) of the title compound as a white solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. customthe volatiles were removed under reduced pressure
  3. filtrationThe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-5cfa2065b1fe406cae35342886381f3c
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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