Boron tribromide → HCID 68815892, compound

HRID 731049Notes

Reaction equation

HRID 731049 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH3:22])[C:17]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]3=2)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:22][N:18]1[C:19]2[CH:20]=[CH:21][C:9]([C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=3)=[CH:10][C:11]=2[C:12]2[CH2:13][CH2:14][CH2:15][CH2:16][C:17]1=2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68815889HCID 68815889, compound

Product 1

HCID 68815892HCID 68815892, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The desired product was prepared using a procedure similar to step 4 of example 3. Thus, 6-(4-methoxy-phenyl)-9-methyl-2,3,4,9-tetrahydro-1H-carbazole (1.214 g, 4.166 mmol) was reacted with BBr3 (5.0 ml of a 1M solution in CH2Cl2) to give the product (0.382 g, 1.377 mmol, 33%) as a brown oil. 1H NMR (DMSO-d6) δ 1.76-1.80 (m, 2H), 1.83-1.90 (m, 2H), 2.65 (t, J=5.8 Hz, 2H), 2.71 (t, J=5.8 Hz, 2H), 3.59 (s, 3H), 6.81 (d, J=8.6 Hz, 2H), 7.26 (dd, J=1.2, 8.4 Hz, 1H), 7.35 (d, J=8.4 Hz, 1H), 7.45 (d, J=8.6 Hz, 2H), 7.50 (s, 1H), 9.31 (s, 1H); [ESI(+)], m/z 276 (M+H)+.

Sources & evidence

ORD record
ord-c41b7887d2444929aee939203d52c492
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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