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

HRID 47845

反応式

HRID 47845 の反応式
[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]

参加物

5

反応物 3

HCID 962WaterHCID 235373-Chloro-4-acetotoluidideHCID 24408Bromine2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

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];

後処理

  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

出典と根拠

ORDレコード
ord-e11d128447924916b087882788ace551
出典データセット
uspto-grants-2004_03
特許番号
US06699861B1

関連ノート

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