Water → 4-Bromo-2-ethyl-6-methylaniline

HRID 2250180Notes

Reaction equation

HRID 2250180 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[NH2:10])[CH3:2].O.[Br:12]Br>Cl>[Br:12][C:7]1[CH:6]=[C:5]([CH3:9])[C:4]([NH2:10])=[C:3]([CH2:1][CH3:2])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 324852-Ethyl-6-methylaniline

Product 1

HCID 9607614-Bromo-2-ethyl-6-methylaniline

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

2-Ethyl-6-methyl-phenylamine (14 mL, 100 mmol) was dissolved in concentrated hydrochloric acid (30 mL) and water (220 mL) and cooled to 0° C. To this was added bromine (5.1 mL, 1 equiv.) dropwise. There was rapid formation of a white precipitate. The precipitate was filtered and washed with diethyl ether. The precipitate was suspended in water and neutralized with aqueous potassium carbonate. An oil formed which was extracted into diethyl ether. The ethereal was dried over potassium carbonate, filtered, and concentrated to give 7.0 g (33%) as a purple oil which was used without purification. Mass spec.: 214.01 (MH)+.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with diethyl ether
  3. customAn oil formed which
  4. extractionwas extracted into diethyl ether
  5. dry with materialThe ethereal was dried over potassium carbonate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give 7.0 g (33%) as a purple oil which
  9. customwas used without purification

Sources & evidence

ORD record
ord-c82b35f64f844941ad19de925973818a
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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