Dichloromethane → 9-(4-Hydroxy-phenyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-ol

HRID 418959Notes

Reaction equation

HRID 418959 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[CH2:13][CH:12]([C:17]1[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.C(Cl)Cl.B(Br)(Br)Br>C(OCC)(=O)C>[OH:23][C:20]1[CH:19]=[CH:18][C:17]([CH:12]2[CH2:13][C:14]3[CH:15]=[CH:16][C:3]([OH:2])=[CH:4][C:5]=3[CH:6]3[CH:11]2[CH2:10][CH2:9][CH2:8][CH2:7]3)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 666521086-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

Product 1

HCID 666527059-(4-Hydroxy-phenyl)-4b,5,6,7,8,8a,9,10-octahydro-phenanthren-3-olYield 72%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Combine 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene (132.1 mg, 0.41 mmol), methylene chloride (4.0 mL), boron tribromide (0.16 mL, 1.64 mmol) at 0° C., and stir under a nitrogen atmosphere. After 1.5 hours, add ethyl acetate to reaction mixture, quench reaction with sat ammonium chloride solution (aq). Wash organic layer with brine, dry over sodium sulfate, and concentrate in vacuo. Flash chromatograph to yield the titled compound (86.7 mg, 72%) as a white solid. 1H NMR (DMSO): 9.15 (s, 1H), 9.00 (s, 1H), 7.08 (d, 2H, J=8.8 Hz), 6.93 (d, 1H, J=8.4 Hz), 6.70 (m, 3H), 6.52 (dd, 1H, J=8.4, 2.2 Hz), 3.05 (m, 3H), 2.65 (m, 1H), 2.34 (d, 1H, J=12.8 Hz), 1.88 (m, 1H), 1.55 (m, 2H), 1.37 (m, 1H), 1.05 (m, 4H); MS m/z 293 (M−1).

Workup

  1. customto reaction mixture
  2. customquench
  3. customreaction with sat ammonium chloride solution (aq)
  4. dry with materialWash organic layer with brine, dry over sodium sulfate
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-cb6841bb53394cb4a02aa72cebac286a
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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