Bromine → 2-Bromo-4-methoxy-5-methyl-indan-1-one

HRID 389320Notes

Reaction equation

HRID 389320 reaction equation
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][C:7]2=[O:13].[Br:14]Br.C(=O)(O)[O-].[Na+]>C(O)(=O)C.Br>[Br:14][CH:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:12])[C:3]=2[O:2][CH3:1])[C:7]1=[O:13]

Participants

6

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 552973254-Methoxy-5-methyl-indan-1-one

Product 1

HCID 668127112-Bromo-4-methoxy-5-methyl-indan-1-oneYield 44.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 260Hydrogen BromideSolvent

Conditions

Temperature
22.5 °C

Procedure

To a stirred solution of 4-Methoxy-5-methyl-indan-1-one (5.0 gm, 0.0284 mole) in Acetic acid (65 ml) and Hydrobromic acid (1 ml), a solution of Bromine (1.47 ml, 0.0284 mole) in 5 ml Acetic acid was added at 10-20° C. The reaction mixture was stirred at 20-25° C. for an hour. Then it was poured into saturated solution of Sodium bicarbonate and extracted with Diethyl ether (3×100 ml). The organic layer was dried over Sodium sulphate, distilled under vacuum to give crude product which was purified over column chromatography using Ethyl acetate:Hexane (5:95) as a mobile phase. The collected fractions were distilled to give 3.2 gm of desired product as a viscous oil.

Workup

  1. extractionextracted with Diethyl ether (3×100 ml)
  2. dry with materialThe organic layer was dried over Sodium sulphate
  3. distillationdistilled under vacuum
  4. customto give crude product which
  5. customwas purified over column chromatography
  6. distillationThe collected fractions were distilled

Sources & evidence

ORD record
ord-78b60c0db0cb467193aa5b0548e8db8b
Source dataset
uspto-grants-2013_02
Patent number
US08378118B2

Reaction notes

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