Dichloromethane → 4-bromo-2-(cyclohexylmethyl)-3,5,6,7-tetrahydro-s-indacen-1(2H)-one

HRID 538859Notes

Reaction equation

HRID 538859 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].ClCCl.[CH:8]1([CH2:14][CH:15]2[CH2:26][C:25]3[C:17](=[CH:18][C:19]4[CH2:20][CH2:21][CH2:22][C:23]=4[CH:24]=3)[C:16]2=[O:27])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[Br:28]Br>>[CH:8]1([CH2:14][CH:15]2[CH2:26][C:25]3[C:17](=[CH:18][C:19]4[CH2:20][CH2:21][CH2:22][C:23]=4[C:24]=3[Br:28])[C:16]2=[O:27])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 24408BromineHCID 6451240Aluminum(III) ChlorideHCID 666155982-(Cyclohexylmethyl)-3,5,6,7-tetrahydro-s-indacen-1(2H)-one

Product 1

HCID 666157014-bromo-2-(cyclohexylmethyl)-3,5,6,7-tetrahydro-s-indacen-1(2H)-one

Conditions

Temperature
0 °C

Procedure

To a mixture of 40.9 g (0.305 mol) of AlCl3 in 180 ml of dichloromethane 32.7 g (0.122 mol) of 2-(cyclohexylmethyl)-3,5,6,7-tetrahydro-s-indacen-1(2H)-one was added. To this mixture cooled to 0° C. 21.5 g (0.134 mol) of bromine was added dropwise by vigorous stirring for 45 min at 0-5° C. The resulting mixture was stirred for 12 h at ambient temperature and then poured on 1000 cm3 of ice. The organic layer was separated, and the aqueous layer was extracted with 3×200 ml of dichloromethane. The combined organic extract was dried over Na2SO4 and then evaporated to dryness. This product was further used without an additional purification. Yield 39.5 g (93%).

Workup

  1. additionwas added
  2. stirringThe resulting mixture was stirred for 12 h at ambient temperature
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with 3×200 ml of dichloromethane
  5. extractionThe combined organic extract
  6. dry with materialwas dried over Na2SO4
  7. customevaporated to dryness
  8. customThis product was further used without an additional purification

Sources & evidence

ORD record
ord-fcf1d55813314427b0c2d3d5ca4f02e3
Source dataset
uspto-grants-2014_10
Patent number
US08865848B2

Reaction notes

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