N-bromobutanimide → 1-(4-Amino-3-bromo-phenyl)-cyclohexane carbonitrile

HRID 2408505Notes

Reaction equation

HRID 2408505 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C1C(=O)N([Br:23])C(=O)C1>C(Cl)Cl>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][C:7]=1[Br:23]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 498745261-(4-Aminophenyl)cyclohexanecarbonitrile

Product 1

HCID 589937601-(4-Amino-3-bromo-phenyl)-cyclohexane carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared from 1-(4-amino-phenyl)-cyclohexane carbonitrile (as prepared in the previous step) by bromination with NBS according to the procedure in Example 4, step (b), replacing CH3CN with CH2Cl2. 1H-NMR (CDCl3; 400 MHz): δ 7.49 (d, 1H, J=2.0 Hz), 7.23 (dd, 1H, J=8.4, 2.0 Hz), 6.76 (d, 1H, J=8.4 Hz), 2.16-2.08 (m, 2H), 1.90-1.73 (m, 8H).

Sources & evidence

ORD record
ord-bb7316981032420e8788f85fe663082c
Source dataset
uspto-grants-2014_08
Patent number
US08815867B2

Reaction notes

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