2-Bromo-4,6-dimethylaniline → N-(2-Bromo-4,6-dimethyl-phenyl)-2-(4-fluoro-phenyl)-acetamide

HRID 1820135Notes

Reaction equation

HRID 1820135 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[NH2:4].[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C:19](Cl)=[O:20])=[CH:14][CH:13]=1>C(#N)C>[Br:1][C:2]1[CH:8]=[C:7]([CH3:9])[CH:6]=[C:5]([CH3:10])[C:3]=1[NH:4][C:19](=[O:20])[CH2:18][C:15]1[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 1705792-Bromo-4,6-dimethylanilineHCID 37449884-Fluorophenylacetyl chloride

Product 1

HCID 11530121N-(2-Bromo-4,6-dimethyl-phenyl)-2-(4-fluoro-phenyl)-acetamideYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

2-Bromo-4,6-dimethyl-aniline (600 mg) and (4-fluoro-phenyl)-acetyl chloride (543 mg) were dissolved in acetonitrile (6 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. The reaction was cooled to 0° C., the product filtered off and washed with cold acetonitrile (50 mL) affording 665 mg (66% yield) of the title compound as a white solid. LC-MS (m/z) 337 (MH+); tR=2.93, (UV, ELSD) 90%, 98%. 1H NMR (500 MHz, DMSO-d6): 2.05 (s, 6H), 2.25 (s, 3H), 3.63 (s, 2H), 7.05 (b, 1H), 7.15 (dt, 2H), 7.32 (b, 1H), 7.40 (dt, 2H), 9.67 (s, 1H).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. filtrationthe product filtered off
  3. washwashed with cold acetonitrile (50 mL)

Sources & evidence

ORD record
ord-beff1d8e028c49678c0df7bcd2150be6
Source dataset
uspto-grants-2009_10
Patent number
US07601870B2

Reaction notes

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