Actarit → 4-(Acetylamino)-3-bromobenzeneacetic acid

HRID 1733017Notes

Reaction equation

HRID 1733017 reaction equation
[Br:1]Br.[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][CH:8]=1)(=[O:5])[CH3:4]>C(O)(=O)C.O>[C:3]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=[O:15])=[CH:9][C:8]=1[Br:1])(=[O:5])[CH3:4]

Participants

5

Reactant 2

HCID 2018ActaritHCID 24408Bromine

Product 1

HCID 203034124-(Acetylamino)-3-bromobenzeneacetic acidYield 55.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

102.2 g (0.64 mole) of bromine are added dropwise at room temperature, with stirring, to a suspension of 100 g (0.52 mole) of 4-acetamidophenylacetic acid in 1 liter of glacial acetic acid; during this dropwise addition, a solution forms intermittently. Subsequently, heating to 60° C. is effected for 12 hours, followed by cooling to room temperature, diluting with 2 liters of water and extracting three times with diethyl ether. The organic phase is washed with sodium hydrogen sulfite solution and water, dried and concentrated to dryness. The residue is recrystallized from acetonitrile to yield 78 g (55.3% of theory) of 4-acetamido-3-bromophenylacetic acid (m.p. 157° to 159° C.).

Workup

  1. additionduring this dropwise addition
  2. temperatureby cooling to room temperature
  3. extractionextracting three times with diethyl ether
  4. washThe organic phase is washed with sodium hydrogen sulfite solution and water
  5. customdried
  6. concentrationconcentrated to dryness
  7. customThe residue is recrystallized from acetonitrile

Sources & evidence

ORD record
ord-6379283ab012444d86f657a001caeb6e
Source dataset
uspto-grants-1980_12
Patent number
US04239901

Reaction notes

Loading…