Hydrogen Bromide → 2-Phenylindan-5-ol

HRID 31242Notes

Reaction equation

HRID 31242 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 methylenechloride. 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 methylenechloride
  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-61b11eb5ac0c4c53932e0f7da639cd2f
Source dataset
uspto-grants-2008_09
Patent number
US07425568B2

Reaction notes

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