Boron tribromide → HCID 68813887, compound

HRID 731083Notes

Reaction equation

HRID 731083 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[C:11]([CH3:25])=[C:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:13]3[CH3:18])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:18][N:13]1[C:14]2[C:10](=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=3)[CH:17]=[CH:16][CH:15]=2)[C:11]([CH3:25])=[C:12]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68815374HCID 68815374, compound

Product 1

HCID 68813887HCID 68813887, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The desired product was prepared using a procedure similar to step 4 of example 3. Thus, 4-(4-methoxy-phenyl)-1,3-dimethyl-2-phenyl-1H-indole (1.227 g, 3.747 mmol) was reacted with BBr3 (4.5 ml of a 1M solution in CH2Cl2) to give the product (0.751 g, 2.396 mmol, 64%) as a white solid, mp 132-134° C. 1H NMR (DMSO-d6) δ 1.71 (s, 3H), 3.57 (s, 3H), 6.78-6.83 (m, 3H), 7.15-7.19 (m, 3H), 7.40-7.46 (m, 4H), 7.52 (t, J=7.2 Hz, 2H), 9.39 (s, 1H); IR (solid) 3480, 3430, 2920, 1605, 1520, 1480, 1450, 1310, 1270, and 1180 cm−1; [ESI(+)], m/z 314 (M+H)+; Anal. Calcd. for C22H19NO: C, 84.31; H, 6.11; N, 4.47; Found: C, 84.17; H, 6.10; N, 4.42.

Sources & evidence

ORD record
ord-e34a22f800764712b97d353a8583f8fe
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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