Boron tribromide → HCID 68815835, compound

HRID 731029Notes

Reaction equation

HRID 731029 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:12]3[CH3:25])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:18][N:14]1[C:15]2[C:11](=[CH:10][C:9]([C:6]3[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=3)=[CH:17][CH:16]=2)[C:12]([CH3:25])=[C:13]1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68814224HCID 68814224, compound

Product 1

HCID 68815835HCID 68815835, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The desired product was prepared using a procedure similar to step 4 of example 3. Thus, 5-(4-methoxy-phenyl)-1,3-dimethyl-2-phenyl-1H-indole (0.560 g, 1.710 mmol) was reacted with BBr3 (2.1 ml of a 1M solution in CH2Cl2) to give the desired product (0.484 g, 1.544 mmol, 90%) as a white solid, mp 148-150° C. 1H NMR (DMSO-d6) δ 2.24 (s, 3H), 3.60 (s, 3H), 6.84 (d, J=8.6 Hz, 2H), 7.40 (dd, J=1.4, 8.4 Hz, 1H), 7.44-7.47 (m, 4H), 7.50-7.56 (m, 4H), 7.68 (s, 1H), 9.37 (s, 1H); IR (solid) 3350, 3050, 1590, 1520, 1460, and 1230 cm−1; [ESI(+)], m/z 314 (M+H)+; Anal. Calcd. for C22H19NO: C, 84.31; H, 6.11; N, 4.47; Found: C, 84.21; H, 6.37; N, 4.38.

Workup

  1. customThe desired product was prepared

Sources & evidence

ORD record
ord-d10ea5266cb04f72ba8df554266e539e
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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