Water → N-(2-Bromo-5-chloro-4-methylphenyl)acetamide

HRID 47845

반응식

HRID 47845 반응식
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([Cl:12])[CH:6]=1)(=[O:3])[CH3:2].[Br:13]Br.O>C(O)(=O)C>[C:1]([NH:4][C:5]1[C:10]([Br:13])=[CH:9][C:8]([CH3:11])=[C:7]([Cl:12])[CH:6]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 235373-Chloro-4-acetotoluidideHCID 24408Bromine2회

생성물 1

HCID 10989098N-(2-Bromo-5-chloro-4-methylphenyl)acetamide수율 48%

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

To a solution of 4-acetamido-2-chlorotoluene (89.2 g, 0.486 mol) in glacial acetic acid (480 ml) that was stirred with an overhead mechanical stirrer and under argon was dropwise added bromine (28.5 ml) during a period of 2 h while the temperature of the reaction mixture was kept below 15° C. by using an ice-bath. Stirring was continued for a further 1.5 h after the addition of bromine, under an argon atmosphere. Then the brownish reaction mixture was poured into ice-water (1.8 lt), with the aid of water (1 lt), washed with water (6 lt), and dried in vacuo over P2O5. Purification by recrystallisation from acetonitrile afforded the desired product as a white crystals (61.5 g, 48%), mp 154-155° C.; 1H-NMR (CDCl3) 2.24, 2.32 (2×s, 6H, 2×CH3), 7.40, 7.73 (2×s, 2H, 3-H, 6-H), 7.49 (br s, 1H, CONH); MS (FAB, m/z): 262, 264, 266 [(M+H)+, 80%, 100%, 25% respectively; BrCl isotopic pattern];

후처리

  1. customof 2 h
  2. customwas kept below 15° C.
  3. customThen the brownish reaction mixture
  4. washwashed with water (6 lt)
  5. dry with materialdried in vacuo over P2O5
  6. customPurification
  7. customby recrystallisation from acetonitrile

출처 및 근거

ORD 기록
ord-e11d128447924916b087882788ace551
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699861B1

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