Acetic Acid → 5-Acetamido-6-bromoindan

HRID 1289217Notes

Reaction equation

HRID 1289217 reaction equation
[Br:1]Br.[C:3]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH2:11][CH2:10]2)(=[O:5])[CH3:4].C(O)(=O)C>O>[C:3]([NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[Br:1])[CH2:12][CH2:11][CH2:10]2)(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 583823N-(2,3-Dihydro-1H-inden-5-yl)acetamide

Product 1

HCID 104000345-Acetamido-6-bromoindan

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bromine (105 g) was added dropwise to a stirred mixture of 5-acetamidoindan (104.5 g) and acetic acid (400 ml), the rate of addition being such that the temperature of the reaction mixture was maintained in the range 20° to 25° C. The mixture was poured into a mixture (2 L) of ice and water. The precipitate was isolated, washed with water and dried. There was thus obtained 5-acetamido-6-bromoindan (143 g), m.p. 138° C.

Workup

  1. additionthe rate of addition
  2. temperaturewas maintained in the range 20° to 25° C
  3. customThe precipitate was isolated
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-886d969533eb4a7997c5a76c66e31ebf
Source dataset
uspto-grants-1998_05
Patent number
US05747499

Reaction notes

Loading…