Hydrogen Bromide → 4-(2-bromoacetyl)benzoic Acid

HRID 2260481Notes

Reaction equation

HRID 2260481 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br:13]Br.Br>C(O)(=O)C>[Br:13][CH2:2][C:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 114704-Acetylbenzoic AcidHCID 24408Bromine2×

Product 1

HCID 27568364-(2-bromoacetyl)benzoic Acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
45 °C

Procedure

2.0 g (12.2 mmole) of 4-acetyl benzoic acid was added to 90 ml of acetic acid in a 500 ml erlenmeyer flask and heated at 45° C. until dissolved. Maintaining the temperature at 45° C., 1.95 g (12.2 mmole, 0.61 ml) of bromine dissolved in ~2 ml acetic acid was added slowly over 1 hour with vigorous stirring. The reaction required an induction period of several minutes before proceeding, which became evident by the loss of the red bromine color and the evolution of HBr. The product, BABA (Modifying Reagent II), was precipitated on ice, collected by filtration and recrystallized 3 times from hot (75° C.) ethanol.

Workup

  1. dissolutionuntil dissolved
  2. temperatureMaintaining the temperature at 45° C.
  3. additionwas added slowly over 1 hour with vigorous stirring
  4. customThe reaction
  5. customan induction period of several minutes
  6. customThe product, BABA (Modifying Reagent II), was precipitated on ice
  7. filtrationcollected by filtration
  8. customrecrystallized 3 times from hot (75° C.) ethanol

Sources & evidence

ORD record
ord-0713b179c4c246518ddd5a51f9ecacba
Source dataset
uspto-grants-1995_12
Patent number
US05478729

Reaction notes

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