Acetic Acid → 2-Bromo-4-chloro-6-methylbenzenamine

HRID 913826

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HRID 913826 반응식
[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.[Br-:10].[K+].C(O)(=O)C.B1([O-])OO1.O.O.O.O.[Na+].C(=O)(O)[O-].[Na+]>N.N.N.N.N.N.O.O.O.O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O.O[Mo](O)(=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O>[Br:10][C:7]1[CH:8]=[C:2]([Cl:1])[CH:3]=[C:4]([CH3:9])[C:5]=1[NH2:6]

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 72514-Chloro-2-toluidineHCID 253877Potassium BromideHCID 516892Sodium BicarbonateHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

생성물 1

HCID 205437542-Bromo-4-chloro-6-methylbenzenamine

시약·촉매·용매 2

HCID 16211167Ammonium paramolybdate tetrahydrate촉매HCID 962Water용매

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온도
0 °C

실험 절차

4-Chloro-2-methylaniline (1.0 g, 7.06 mmol), potassium bromide (1.01 g, 8.47 mmol), and ammonium heptamolybdate tetrahydrate (87 mg, 0.07 mmol) were suspended in acetic acid (7 mL, 122 mmol) and cooled to 0° C. The reaction was treated with sodium perborate tetrahydrate (1.2 g, 7.77 mmol), stirred at 0° C. for 30 min, and at room temperature for 2 h. The mixture was poured into water, neutralized with saturated sodium bicarbonate and extracted with ethyl acetate (2×). The organic layers were pooled together, washed with brine (2×), dried over sodium sulfate, and concentrated to afford 1.2 g (78%). 1H-NMR (CDCl3, 500 MHz) δ 7.28 (s, 1H), 6.97 (s, 1H), 4.03 (bs, 2H), 2.17 (s, 3) Mass spec.: 221.90 (MH)+.

후처리

  1. waitat room temperature for 2 h
  2. extractionextracted with ethyl acetate (2×)
  3. washwashed with brine (2×)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto afford 1.2 g (78%)

출처 및 근거

ORD 기록
ord-b3bb722067144d10a04789b67aeacb86
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026257B2

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