Bromine → 7-Bromo-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

HRID 418935Notes

Reaction equation

HRID 418935 reaction equation
[CH3:1][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][CH3:24])=[CH:19][CH:18]=1)[CH:11]1[CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10]1.[Br:25]Br>C(Cl)Cl>[Br:25][C:16]1[CH:15]=[C:14]2[C:5]([CH:6]3[CH:11]([CH:12]([C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)[CH2:13]2)[CH2:10][CH2:9][CH2:8][CH2:7]3)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 24408BromineHCID 666521086-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

Product 1

HCID 666520557-Bromo-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthreneYield 124.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene (chiral) (0.02 g, 0.32 mmol) and methylene chloride (10 ml) and add bromine (0.0162 ml, 0.32 mmol) at 0-5° C. over 15 minutes. Stir as such one hour. Remove volatiles in vacuo at 40° C. to yield the titled compound (0.16 g, 100%). 1H NMR (CDCl3): 7.38 (s, 1H), 7.25 (d, J=8.8 Hz, 2H), 6.9 (m, 3H), 3.93 (s, 3H), 3.85 (s, 3H), 3.2 (m, 3H), 2.85 (dd, J=4 and 11, 1H), 2.48 (d, J=14 Hz, 1H), 2.06 (m, 1H), 1.8-0.8 (m, 7H).

Sources & evidence

ORD record
ord-5f8a23497f004872a63b2d3a191ba5f5
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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