Boron tribromide → 4-(9-Benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-yl)-phenol

HRID 731043Notes

Reaction equation

HRID 731043 reaction equation
[CH2:1]([N:8]1[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[C:12]([C:21]1[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=1)[CH:13]=2)[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:9]2[CH:10]=[CH:11][C:12]([C:21]3[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=3)=[CH:13][C:14]=2[C:15]2[CH2:16][CH2:17][CH2:18][CH2:19][C:20]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 688167799-Benzyl-6-(4-methoxy-phenyl)-2,3,4,9-tetrahydro-1H-carbazole

Product 1

HCID 688142534-(9-Benzyl-6,7,8,9-tetrahydro-5H-carbazol-3-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, 9-benzyl-6-(4-methoxy-phenyl)-2,3,4,9-tetrahydro-1H-carbazole (1.930 g, 5.252 mmol) was reacted with BBr3 (6.3 ml of a 1M solution in CH2Cl2) to give the product (0.840 g, 2.377 mmol, 45%) as a pale-green foam. 1H NMR (DMSO-d6) δ 1.78-1.85 (m, 4H), 2.63-2.70 (m, 4H), 5.32 (s, 2H), 6.81 (d, J=8.4 Hz, 2H), 7.03 (d, J=7.5 Hz, 2H), 7.19-7.23 (m, 2H), 7.28 (t, J=7.6 Hz, 2H), 7.36 (d, J=8.6 Hz, 1H), 7.44 (d, J=8.6 Hz, 2H), 7.53 (s, 1H), 9.32 (s, 1H); [ESI(+)], m/z 354 (M+H)+.

Sources & evidence

ORD record
ord-cfae29c47e0f4da186b94f3c4426e2f1
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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