Boron tribromide → 4-(1-Benzyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenol

HRID 731090Notes

Reaction equation

HRID 731090 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([O:23]C)=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:10]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[C:9]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)=[CH:14][CH:15]=2)[C:10]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[C:9]1[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 688143491-Benzyl-5-(4-methoxy-phenyl)-3-pentyl-2-phenyl-1H-indole

Product 1

HCID 688155514-(1-Benzyl-3-pentyl-2-phenyl-1H-indol-5-yl)-phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The desired product was prepared using a procedure similar to step 4 of example 3. Thus, 1-benzyl-5-(4-methoxy-phenyl)-3-pentyl-2-phenyl-1H-indole (0.708 g, 1.54 mmol) was reacted with BBr3 (1.9 ml of a 1M solution in CH2Cl2) to give the product (0.609 g, 1.367 mmol, 89%) as a viscous oil. 1H NMR (DMSO-d6) δ 0.76 (t, J=69 Hz, 3H), 1.13-1.22 (m, 4H), 1.53-1.59 (m, 2H), 2.67 (t, J=7.3 Hz, 2H), 5.26 (s, 2H), 6.82-6.85 (m, 4H), 7.14 (t, J=7.2 Hz, 1H), 7.19 (t, J=6.9 Hz, 2H), 7.29-7.37 (m, 4H), 7.41-7.49 (m, 5H), 7.70 (d, J=1.2 Hz, 1H), 9.37 (s, 1H); [ESI(+)], m/z 446 (M+H)+;

Sources & evidence

ORD record
ord-e0032390912440caa1f01aa96dc163cf
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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