Potassium Bromide → 2-Bromo-6-methyl-4-(trifluoromethyl)aniline

HRID 913807

反応式

HRID 913807 の反応式
[CH3:1][C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[Br-:13].[K+].B1([O-])OO1.O.O.O.O.[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C.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:13][C:5]1[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:2]([CH3:1])[C:3]=1[NH2:4]

参加物

8

反応物 4

HCID 253877Potassium Bromide4 回HCID 516892Sodium BicarbonateHCID 137504374-Amino-3-methylbenzotrifluorideHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate4 回

生成物 1

HCID 534166792-Bromo-6-methyl-4-(trifluoromethyl)aniline

試薬・触媒・溶媒 3

HCID 16211167Ammonium paramolybdate tetrahydrate触媒4 回HCID 176Acetic Acid溶媒HCID 962Water溶媒

実験手順

To a suspension of 2-methyl-4-(trifluoromethyl)aniline (7.78 g, 44.4 mmol), potassium bromide (1.59 g, 13.3 mmol), and ammonium heptamolybdate tetrahydrate (140 mg, 0.111 mmol) in acetic acid (40 mL) at room temperature (in a room temperature waterbath) was added sodium perborate tetrahydrate (1.88 g, 12.2 mmol). After 10 min, the reaction was treated with an additional portion of potassium bromide (1.59 g, 13.3 mmol), ammonium heptamolybdate tetrahydrate (140 mg, 0.111 mmol), and sodium perborate tetrahydrate (1.88 g, 12.2 mmol). After 10 min, the reaction was treated with an additional portion of potassium bromide (1.59 g, 13.3 mmol), ammonium heptamolybdate tetrahydrate (140 mg, 0.111 mmol), and sodium perborate tetrahydrate (1.88 g, 12.2 mmol). After 10 min, the reaction was treated with an additional portion of potassium bromide (1.59 g, 13.33 mmol), ammonium heptamolybdate tetrahydrate (140 mg, 0.111 mmol), and sodium perborate tetrahydrate (1.88 g, 12.2 mmol). After 1 h, the reaction was treated with a final portion of everything in half the amounts of the previous additions. After 1 h, the mixture was poured into water, neutralized with solid sodium bicarbonate, extracted into diethyl ether, washed with water, then brine, dried over magnesium sulfate, and concentrated to give 11.3 g (100%) as an oil. 1H-NMR (CDCl3, 500 MHz) δ 7.56 (s, 1H), 7.23 (s, 1H), 4.36 (bs, 2H), 2.23 (s, 3H); 13C-NMR (CDCl3, 126 MHz) δ 145.3, 127.7 (q, J=3.8 Hz), 126.4 (q, J=3.8 Hz), 124.0 (q, J=272 Hz), 120.6 (q, J=34 Hz), 108.2, 18.3. Mass spec.: 253.95 (MH)+.

後処理

  1. waitAfter 10 min
  2. waitAfter 10 min
  3. waitAfter 1 h
  4. additionthe reaction was treated with a final portion of everything in half the amounts of the previous additions
  5. waitAfter 1 h
  6. extractionextracted into diethyl ether
  7. washwashed with water
  8. dry with materialbrine, dried over magnesium sulfate
  9. concentrationconcentrated
  10. customto give 11.3 g (100%) as an oil

出典と根拠

ORDレコード
ord-2d55ca11fb7f49f89ff170d3ce86f66e
出典データセット
uspto-grants-2011_09
特許番号
US08026257B2

関連ノート

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