Benzyl Bromide → 9-Benzyl-6-bromo-2,3,4,9-tetrahydro-1H-carbazole

HRID 731041Notes

Reaction equation

HRID 731041 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH2:7][CH2:6][C:5]2=1.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C>[CH2:15]([N:11]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[C:4]2[C:12]1=[CH:13][CH:14]=[C:2]([Br:1])[CH:3]=2)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 2688776-Bromo-1,2,3,4-tetrahydrocarbazole

Product 1

HCID 688159639-Benzyl-6-bromo-2,3,4,9-tetrahydro-1H-carbazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The desired product was prepared using a procedure similar to step 2 of example 3. Thus, 6-bromo-2,3,4,9-tetrahydro-1H-carbazole (1.876 g, 7.5 mmol) was reacted with k-t-butoxide (0.884 g, 7.875 mmol) and benzyl bromide (1.352 g, 7.875 mmol) in DMF (20 ml) to give the product (2.225 g, 6.539 mmol, 87%) as an oily, yellow solid. 1H NMR (DMSO-d6) δ 1.74-1.83 (m, 4H), 2.61-2.64 (m, 4H), 5.32 (s, 2H), 6.99 (d, J=7.6 Hz, 2H), 7.11 (dd, 1.8, 8.7 Hz, 1H), 7.21 (t, J=7.2 Hz, 1H), 7.27 (t, J=7.3 Hz, 2H), 7.33 (d, J=8.6 Hz, 1H), 7.55 (d, J=1.5 Hz, 1H); [ESI(+)], m/z 340/342 (M+H)+.

Sources & evidence

ORD record
ord-dea004d249c442918e6f86b56f0f100d
Source dataset
uspto-grants-2009_09
Patent number
US07582773B2

Reaction notes

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