Water → 2-(2-Bromo-5-methoxyphenyl)acetic acid

HRID 1270785Notes

Reaction equation

HRID 1270785 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([Br:12])=[C:7]([CH2:9][C:10]#N)[CH:8]=1.[OH-:13].[Na+].[OH2:15]>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([Br:12])=[C:7]([CH2:9][C:10]([OH:15])=[O:13])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 6396662-(2-Bromo-5-methoxyphenyl)acetonitrile2×

Product 1

HCID 106340802-(2-Bromo-5-methoxyphenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Methoxy-2-bromophenylacetonitrile (52.8 g, 0.23 mol) is dissolved in ethanol (250 mL) and stirred at room temperature. Sodium hydroxide (9.3 g, 0.47 mol) is dissolved in water (150 mL) and added to the solution of the nitrile. The mixture is heated to reflux temperature for 12 hours and then cooled to room temperature. Most of the ethanol is removed using a rotary evaporator and the residual aqueous solution adjusted to pH 4 with 3 N HCl. The solid which forms is isolated by filtration and washed with water. Air drying gives 5-methoxy-2-bromophenylacetic acid.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux temperature for 12 hours
  3. temperaturecooled to room temperature
  4. customMost of the ethanol is removed
  5. customa rotary evaporator
  6. customThe solid which forms is isolated by filtration
  7. washwashed with water
  8. customAir drying

Sources & evidence

ORD record
ord-d23f8ef1f47e4505abf300f211735641
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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