Aniline → HCID 9816037, compound

HRID 1595010Notes

Reaction equation

HRID 1595010 reaction equation
[C:1](ON=O)(C)([CH3:3])[CH3:2].C(Br)C=C.[N+:12]([C:15]1[CH:21]=[CH:20][C:18](N)=[CH:17][C:16]=1[C:22]([F:25])([F:24])[F:23])([O-:14])=[O:13].NC1C=CC=CC=1>CC#N>[CH2:3]([C:18]1[CH:20]=[CH:21][C:15]([N+:12]([O-:14])=[O:13])=[C:16]([C:22]([F:25])([F:24])[F:23])[CH:17]=1)[CH:1]=[CH2:2]

Participants

6

Reactant 4

HCID 6115AnilineHCID 7841Allyl bromideHCID 10906Tert-Butyl nitrite2×HCID 949554-Nitro-3-(trifluoromethyl)aniline

Product 1

HCID 9816037HCID 9816037, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
14 °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-nitro-3-trifluoromethylaniline (618 mg, 3.0 mmol) was added during 20 minutes, while maintaining the temperature of the reaction mixture between 13-15° 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 25° C. for one hour. The volatile material in the reaction mixture was removed at reduced pressure. Column chromatography (heptane-ethyl acetate 97:3) gave 430 mg (62%) of allyl-4-nitro-3-trifluoromethylbenzene as a light yellow oil. 1H NMR (CDCl3, 400 MHz) δ 7.86, (d, 1H, J=8.3 Hz), 7.65, (d, 1H, J=1.2 Hz), 7.55, (dd, 1H, J=8.3, 1.4 Hz), 6.00-5.89, (m, 1H), 5.26-5.14, (m, 2H), 3.54, (d, 2H, J=6.7 Hz); 13C NMR (CDCl3, 100 MHz) δ 146.5, 135.0, 133.3, 128.5, (q, J=5.0 Hz), 125.8, 124.4, 124.1, 123.8, 121.1, 118.8, 40.0; Anal HRMS Calcd. for C10H8F3NO2 (M): 231.0507. Found: 208.0499.

Workup

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

Sources & evidence

ORD record
ord-1d4278d09dc24d71bd73b54981451c95
Source dataset
uspto-grants-2001_09
Patent number
US06284894B1

Reaction notes

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