p-Toluenesulfonic acid → HCID 58418727, compound

HRID 557495Notes

Reaction equation

HRID 557495 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][CH2:6][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][CH:6]=[CH:7]2

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 58418780HCID 58418780, compound

Product 1

HCID 58418727HCID 58418727, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a hot (110° C.) solution of 2.41 g (10.0 mmol) of 4-(bromomethyl)-1-methoxyindane in 40 ml of toluene 0.20 g of TsOH was added. This mixture was refluxed for 2 hours using a Dean-Stark head. The resulting mixture was passed through short column (4 cm) with silica gel 60 (40-63 μm), the silica gel layer was additionally washed by 20 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 1.98 g (95%) of the title material. Anal. calc. for C10H9Br: C, 57.44; H, 4.34. Found: C, 57.32; H, 4.41. 1H NMR (CDCl3): δ 7.40 (m, 1H, 4-H), 7.29 (m, 1H, 5-H), 7.22 (m, 1H, 6-H), 6.92 (m, 1H, 3-H), 6.63 (m, 1H, 2-H), 4.62 (s, 2H, CH2Br), 3.48 (m, 2H, 1,1′-H).

Workup

  1. temperatureThis mixture was refluxed for 2 hours
  2. washthe silica gel layer was additionally washed by 20 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-4f829767366346d890b39c90300f1543
Source dataset
uspto-grants-2011_11
Patent number
US08058461B2

Reaction notes

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