Acetic Acid → (4-Amino-3-bromophenyl)acetic acid

HRID 1733018Notes

Reaction equation

HRID 1733018 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][C:6]=1[Br:15])(=O)C.[OH-].[Na+].C(O)(=O)C>Cl>[NH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:7][C:6]=1[Br:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 203034124-(Acetylamino)-3-bromobenzeneacetic acid

Product 1

HCID 20303490(4-Amino-3-bromophenyl)acetic acidYield 91.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

30.5 g (0.112 mole) of 4-acetamido-3-bromophenylacetic acid are heated to 100° C. in 100 ml of 6 N hydrochloric acid until a clear solution forms, and the mixture is subsequently kept at 110° C. for one hour. Cooling is effected, followed by rendering alkaline with a solution of sodium hydroxide and acidifying with glacial acetic acid. The thus-formed flocculent precipitate is suction filtered, washed with water and dried to obtain 23.5 g (91.4% of theory) of 4-amino-3-bromophenylacetic acid (m.p. 139° to 140° C.).

Workup

  1. temperatureCooling
  2. filtrationfiltered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-b757cdc7c78541d7b4e2ffb8d19bb4c8
Source dataset
uspto-grants-1980_12
Patent number
US04239901

Reaction notes

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