Hydrogen Bromide → 2-Phenylindan-5-ol

HRID 1455040Notes

Reaction equation

HRID 1455040 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH2:8][CH:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6]2.Br>>[C:12]1([CH:7]2[CH2:6][C:5]3[C:9](=[CH:10][CH:11]=[C:3]([OH:2])[CH:4]=3)[CH2:8]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 127304875-Methoxy-2-phenylindane

Product 1

HCID 179784482-Phenylindan-5-ol

Procedure

Mixture of 5-methoxy-2-phenylindane (200 mg) and concentrated HBr (4 ml) was refluxed for 5.5 h. Reaction mixture was allowed to cool to room temperature and 20 ml of ice water and it was extracted with methylene chloride. The combined organic layers were washed with brine and dried with Na2SO4. The solvents were evaporated to give 2-phenylindan-5-ol. 1H-NMR (400 MHz, d6-DMSO): 9.05 (bs, 1H), 7.3-7.28 (m, 4H), 7.26-7.15 (m, 1H), 7.0 (d, 1H, J 8.1 Hz), 6.64 (d, 1H, J 1.9 Hz), 6.55 (dd, 1H, J 1.9, 8.1 Hz), 3.60 (k, 1H, J 8.6 Hz), 3.18 (m, 2H), 2.86 (dt, 2H, J 8.6, 16 Hz).

Workup

  1. temperaturewas refluxed for 5.5 h
  2. customReaction mixture
  3. extraction20 ml of ice water and it was extracted with methylene chloride
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried with Na2SO4
  6. customThe solvents were evaporated

Sources & evidence

ORD record
ord-f8634254066946b397dd10923e5098d2
Source dataset
uspto-grants-2009_01
Patent number
US07482340B2

Reaction notes

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