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

HRID 913826

反応式

HRID 913826 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 16211167Ammonium paramolybdate tetrahydrate触媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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)+.

後処理

  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%)

出典と根拠

ORDレコード
ord-b3bb722067144d10a04789b67aeacb86
出典データセット
uspto-grants-2011_09
特許番号
US08026257B2

関連ノート

読み込み中…