N-bromobutanimide → 4-Bromo-2-methyl-6-(trifluoromethyl)aniline

HRID 880955Notes

Reaction equation

HRID 880955 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([F:12])([F:11])[F:10])[C:3]=1[NH2:4].[Br:13]N1C(=O)CCC1=O.O.[Cl-].[Na+].O>C(#N)C>[Br:13][C:7]1[CH:6]=[C:5]([C:9]([F:10])([F:11])[F:12])[C:3]([NH2:4])=[C:2]([CH3:1])[CH:8]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 133182332-Amino-3-methylbenzotrifluorideHCID 23713072Sodium chloride dihydrate

Product 1

HCID 674070344-Bromo-2-methyl-6-(trifluoromethyl)anilineYield 95.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a room temperature solution of 2-methyl-6-(trifluoromethyl)aniline (3.0 g, 17 mmol) in acetonitrile (85 mL) was added N-bromosuccinimide (3.0 g, 17 mmol) in small portions over 30 minutes. The reaction was allowed to stir for 1 hour. The reaction was poured into a water/brine mixture and was extracted with ethyl acetate (3×). The combined organics were dried over magnesium sulfate, filtered, and concentrated. Purification by flash column chromatography (0-40% ethyl acetate/heptanes) gave the title compound (4.13 g, 95%) as a brown oil. 1H NMR (400 MHz, CDCl3, δ): 7.42 (d, J=2.34 Hz, 1H), 7.31 (s, 1H), 2.17 (s, 3H).

Workup

  1. extractionwas extracted with ethyl acetate (3×)
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (0-40% ethyl acetate/heptanes)

Sources & evidence

ORD record
ord-f5990fa94d0b47c18ecc7c63f4fc4e84
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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