1,2-Dichlorobenzene → 4-Bromo-2-methyl-1-indanone

HRID 1585974Notes

Reaction equation

HRID 1585974 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([CH3:13])[C:10]([OH:12])=O.ClC1C=CC=CC=1Cl>O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[CH2:8][CH:9]([CH3:13])[C:10]2=[O:12]

Participants

4

Reactant 2

HCID 72391,2-DichlorobenzeneHCID 121623533-(2-Bromophenyl)-2-methylpropanoic acid

Product 1

HCID 105371524-Bromo-2-methyl-1-indanoneYield 56.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

To 52.5 g of 3-(2-bromophenyl)-2-methylpropionic acid (215 mmole) were added 210 g of polyphosphoric acid and 250 ml of o-dichlorobenzene, and the mixture was stirred at 140° C. for 6 hours. The mixture was diluted with 300 ml of water, and the product was extracted with n-hexane and ether, dried and concentrated, and the residual concentrate thus obtained was distilled to give 27.3 g of 4-bromo-2-methylindan-1-one as a colorless oil (yield, 56%).

Workup

  1. extractionthe product was extracted with n-hexane and ether
  2. customdried
  3. concentrationconcentrated
  4. concentrationthe residual concentrate thus
  5. customobtained
  6. distillationwas distilled
  7. customto give

Sources & evidence

ORD record
ord-5bd1c16a27e8439b80a0340b8ec51254
Source dataset
uspto-grants-1999_08
Patent number
US05942459

Reaction notes

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