Aniline → HCID 68533437, compound

HRID 1991091Notes

Reaction equation

HRID 1991091 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[O:11][CH2:12][CH:13]([CH3:15])[CH3:14].Cl[Sn]Cl.C([O-])(O)=O.[Na+].NC1C=CC=CC=1.C1C(=O)N([Br:38])C(=O)C1.C1C[O:42][CH2:41][CH2:40]1>O>[Br:38][C:5]1[CH:4]=[C:3]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:2]([Cl:1])=[CH:7][C:6]=1[NH:8][C:41](=[O:42])[CH3:40]

Participants

8

Reactant 6

HCID 6115AnilineHCID 8028Tetrahydrofuran2×HCID 24479Stannous ChlorideHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 68536085HCID 68536085, compound

Product 1

HCID 68533437HCID 68533437, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.5 g (27.4 mmol) 2-Chloro-1-isobutoxy-4-nitro-benzene was dissolved in 150 ml THF and 30 ml water. After addition of 36.4 g (192 mmol) SnCl2 the reaction mixture was refluxed for 15 minutes. NaHCO3 solution was added, the mixture was extracted with ethyl acetate, dried and concentrated. The crude aniline (5.2 g, 95%) was used without further purification. 2.0 g (10.0 mmol) of the aniline were treated with 1.78 g (10.0 mmol) NBS in 60 ml THF for 20 hours at room temperature. Extraction with ethyl acetate, washings with Na2S2O3 and Na2CO3, drying of the organic phase and removal of solvent yielded 2.75 g of the desired 2-Bromo-5-chloro-4-isobutoxy-aniline.

Workup

  1. temperaturewas refluxed for 15 minutes
  2. extractionthe mixture was extracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated
  5. customThe crude aniline (5.2 g, 95%) was used without further purification
  6. extractionExtraction
  7. washwith ethyl acetate, washings with Na2S2O3 and Na2CO3
  8. customdrying of the organic phase and removal of solvent

Sources & evidence

ORD record
ord-d2dcc6c171c442b6873aeb2467401822
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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