Bromine → 4-Acetamido-3-bromo-2,6-dimethylanisole

HRID 1488452ノート

反応式

HRID 1488452 の反応式
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][CH3:13])=[C:7]([CH3:14])[CH:6]=1)(=[O:3])[CH3:2].[Br:15]Br>C(O)(=O)C>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([O:12][CH3:13])=[C:7]([CH3:14])[C:6]=1[Br:15])(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 24408BromineHCID 218527644-Acetamido-2,6-dimethylanisole

生成物 1

HCID 229056464-Acetamido-3-bromo-2,6-dimethylanisole収率 85.4%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

4-Acetamido-2,6-dimethylanisole (7, 8.6 g, 44.3 mmol) and acetic acid (30 mL) were placed in a round-bottom flask under an argon atmosphere. Bromine (2.7 mL, 44.3 mmol) was added dropwise to the solution, after which the reaction mixture was stirred at room temperature for about 3 h, and then concentrated. The residue was diluted with methylene chloride and carefully washed sequentially with saturated aq. sodium bicarbonate and brine, and dried (MgSO4). Removal of solvents gave a brown-colored solid which was recrystallized from methylene chloride-hexanes to yield 4-acetamido-3-bromo-2,6-dimethylanisole (10.3 g, 85% yield) as an off-white solid, mp 152°-153° C. Spectral data: 1H NMR: δ 2.18 (s, 3H), 2.24 (s, 3H), 2.35 (s, 3H), 3.66 (s, 3H), 7.55 (br s, 1H), 7.9 (s, 1H); 13C NMR: δ 16.1, 16.8, 24.6, 60.1, 114.5, 122.0, 130.5, 131.3, 131.5, 153.6, 168.1; CI-HRMS: calcd. for C11H15BrNO2 (M+H+) 272.0286, fnd. 272.0284.

後処理

  1. concentrationconcentrated
  2. additionThe residue was diluted with methylene chloride
  3. washcarefully washed sequentially with saturated aq. sodium bicarbonate and brine
  4. dry with materialdried (MgSO4)
  5. customRemoval of solvents
  6. customgave a brown-colored solid which
  7. customwas recrystallized from methylene chloride-hexanes

出典と根拠

ORDレコード
ord-2c3c29bb2b8f421d8649d202e963792b
出典データセット
uspto-grants-1997_10
特許番号
US05674876

反応ノート

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