Aniline → Benzene, 1-bromo-4-(2-propenyl)-

HRID 1595016Notes

Reaction equation

C(ON=O)(C)(C)C.[CH2:8]([Br:11])[CH:9]=[CH2:10].Br[C:13]1[CH:19]=[CH:18][C:16](N)=[CH:15][CH:14]=1.NC1C=CC=CC=1>CC#N>[CH2:15]([C:14]1[CH:13]=[CH:19][C:8]([Br:11])=[CH:9][CH:10]=1)[CH:16]=[CH2:18]

Participants

Conditions

Temperature: 32.5 °C

Procedure

To a solution of t-butylnitrite (535 μl, 4.5 mmol) and allyl bromide (3.9 ml, 45.0 mmol) in CH3CN (3 ml), 4-bromoaniline (516 mg, 3.0 mmol) was added during 20 minutes, while maintaining the temperature of the reaction mixture at 30-35° C. At the end of the addition of the aniline, extra t-butylnitrite (180 μl, 1.5 mmol) was added to the reaction mixture which then was stirred at 30° C. for one hour. The volatile material in the reaction mixture was removed at reduced pressure. Column chromatography (pentane) gave 200 mg (34%) of 4-allylbromobenzene as a clear oil. 1H NMR (CDCl3, 400 MHz) δ 7.43, (m, 2H, J=8.3 Hz), 7.08, (m, 2H, J=8.3 Hz), 6.00-5.89, (m, 1H), 5.12-5.05, (m, 2H), 3.35, (d, 2H, J 6.7 Hz); 13C NMR (CDCl3, 100 MHz) δ 139.4, 137.2, 131.9, 130.8, 120.3, 116.7, 40.0; Anal HRMS Calcd. for C9H9Br (M): 195.9888. Found: 195.9887.

Workup

additionwas added to the reaction mixture which
customThe volatile material in the reaction mixture was removed at reduced pressure

Sources & evidence

ORD record: ord-cd5125ded1334c2da89375a310ede069
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06284894B1

Reaction notes

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