Toluene → 7-(bromomethyl)-2-methyl-1H-indene

HRID 1047465Notes

Reaction equation

HRID 1047465 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH:6]([CH3:14])[CH:7]2OC.C1(C)C=CC=CC=1.CC1C=CC(S(O)(=O)=O)=CC=1>>[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][C:6]([CH3:14])=[CH:7]2

Participants

4

Reactant 3

HCID 1140TolueneHCID 6101p-Toluenesulfonic acidHCID 584187504-(Bromomethyl)-1-methoxy-2-methylindane

Product 1

HCID 584187927-(bromomethyl)-2-methyl-1H-indene

Procedure

To a solution of 37.5 g (0.147 mol) of 4-(bromomethyl)-1-methoxy-2-methylindane in 600 ml of toluene 3.12 g (16.4 mmol) of TsOH was added at 110° C. This mixture was refluxed with Dean-Stark trap within 12 min and then passed through short column with Silica Gel 60 (40-63 um, d 90 mm, l 80 mm). The Silica Gel layer was additionally washed by 500 ml of toluene. The combined elute was evaporated to dryness. The product was isolated by flash chromatography on short column with Silica Gel 60 (40-63 um, d 90 mm, l 80 mm; eluent: hexanes). Yield 33.2 g (97%).

Workup

  1. temperatureThis mixture was refluxed with Dean-Stark trap within 12 min
  2. washThe Silica Gel layer was additionally washed by 500 ml of toluene
  3. washThe combined elute
  4. customwas evaporated to dryness
  5. customThe product was isolated by flash chromatography on short column with Silica Gel 60 (40-63 um, d 90 mm, l 80 mm; eluent: hexanes)

Sources & evidence

ORD record
ord-b1898009fe3b4e11a228f9b29e5a17d6
Source dataset
uspto-grants-2013_10
Patent number
US08569532B2

Reaction notes

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