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

HRID 913807

반응식

HRID 913807 반응식
[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]

참가 물질

8

반응물 4

HCID 253877Potassium Bromide4회HCID 516892Sodium BicarbonateHCID 137504374-Amino-3-methylbenzotrifluorideHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate4회

생성물 1

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

시약·촉매·용매 3

HCID 16211167Ammonium paramolybdate tetrahydrate촉매4회HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-2d55ca11fb7f49f89ff170d3ce86f66e
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026257B2

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