p-Toluenesulfonic acid → 7-(bromomethyl)-2-methyl-1H-indene

HRID 557493Notes

Reaction equation

HRID 557493 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.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=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 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 17.9 g (70 mmol) of 4-(bromomethyl)-1-methoxy-2-methylindane in 300 ml of toluene 2.0 g of TsOH was added at 110° C. This mixture was refluxed with Dean-Stark trap within 15 minutes and then passed through short column with silica gel 60 (40-63 μm). The silica gel layer was additionally washed by 200 ml of toluene. The combined elute was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 μm, eluent: hexanes). Yield 15.6 g (96%). Anal. calc. for C11H11Br: C, 59.22; H, 4.97. Found: C, 59.33; H, 5.08. 1H NMR (CDCl3): δ 7.19-7.23 (m, 2H, 4,6-H), 7.10 (m, 1H, 5-H), 6.50 (m, 1H, 3-H), 4.56 (s, 2H, CH2Br), 3.36 (br.s, 2H, 1,1′-H), 2.19 (m, 3H, 2-Me). 13C{1H} NMR (CDCl3): δ 146.6, 146.2, 142.4, 132.0, 127.17, 127.14, 124.4, 120.2, 40.9, 31.7, 16.7.

Workup

  1. temperatureThis mixture was refluxed with Dean-Stark trap within 15 minutes
  2. washThe silica gel layer was additionally washed by 200 ml of toluene
  3. washThe combined elute
  4. customwas evaporated to dryness
  5. customThe product was isolated by flash chromatography on silica gel 60 (40-63 μm, eluent: hexanes)

Sources & evidence

ORD record
ord-1ec34623d4314301b728b653848a13e9
Source dataset
uspto-grants-2011_11
Patent number
US08058461B2

Reaction notes

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