Bromoacetyl chloride → 2-bromo-N-(2,4,6-tribromo-3-methylphenyl)acetamide

HRID 490212Notes

Reaction equation

[CH3:1][C:2]1[C:3]([Br:11])=[C:4]([C:6]([Br:10])=[CH:7][C:8]=1[Br:9])[NH2:5].[Br:12][CH2:13][C:14](Cl)=[O:15]>C1(C)C=CC=CC=1>[Br:12][CH2:13][C:14]([NH:5][C:4]1[C:6]([Br:10])=[CH:7][C:8]([Br:9])=[C:2]([CH3:1])[C:3]=1[Br:11])=[O:15]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 3-methyl-2,4,6-tribromoaniline (4.36 g, 12.7 mmol) in toluene (40 mL) at room temperature was added bromoacetyl chloride (1.20 mL, 14.6 mmol) and the slurry heated to 100° C. for 24 h. The reaction was cooled, filtered, washed with and placed on a high vacuum pump to provide 2.88 g (49%) of the title compound as a white solid. mp 207-209° C.; 1H NMR (300 MHz, DMSO-d6) δ 2.52 (s, 3H) 4.07 (s, 2H) 8.05 (s, 1H) 10.38 (s, 1H); 13C NMR (100 MHz, DMSO-d6) δ 24.2, 28.6, 121.3, 123.4, 127.2, 134.3, 134.9, 137.6, 164.4; MS (DCI/NH3) m/e 482 (M+NH4+); Anal. calcd for C9H7Br4NO: C, 23.26; H, 1.52; N, 3.01. Found: C, 23.30; H, 1.45; N, 2.94.

Workup

temperatureThe reaction was cooled
filtrationfiltered
washwashed with and

Sources & evidence

ORD record: ord-ed5f7dc13acd40b28006934eeed4031a
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528134B2

Reaction notes

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