HCID 12128809、化合物 → 2,5-Dibromo-3,4-dihydro-1(2H)-naphthalenone

HRID 2308205ノート

反応式

HRID 2308205 の反応式
[Br:1][C:2]1(Br)[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[Br:12])[C:3]1=[O:13]>O>[Br:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[Br:12])[C:3]1=[O:13]

参加物

3

反応物 1

HCID 12128809HCID 12128809、化合物

生成物 1

HCID 121288082,5-Dibromo-3,4-dihydro-1(2H)-naphthalenone収率 98.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A clear yellow solution of 5-bromo-3,4-dihydro-1(2H)-naphthalenone (12.09 g, 53.7 mmol) in freshly opened Et2O (220 mL) under an N2 atmosphere was chilled to −5° C. HCl was bubbled in subsurface for 1 min, causing no visible change. The dropwise addition of a solution of Br2 (8.58 g, 53.7 mmol) in CH2Cl2 (20 mL) and Et2O (2 mL) to the vigorously stirring solution of 5-bromo-3,4-dihydro-1(2H)-naphthalenone over 2 h (each drop was allowed to fully decolorize before adding the next) produced a product mixture that assayed by HPLC. Peak area showed 79.4% title compound, 9.5% unreacted 5-bromo-3,4-dihydro-1(2H)-naphthalenone, 0.6% unidentified, and 9.4% 2,2,5-tribromo-1-tetralone. The addition of H2O produced a top light brown organic phase, and a clear, colorless bottom aqueous phase which was separated. After drying with MgSO4, the organic layer was concentrated under vacuum at room temperature to give the crude intermediate title compound as a light brown oil (16.08 g, 98.5%).

後処理

  1. customproduced a top light brown organic phase
  2. customa clear, colorless bottom aqueous phase which was separated
  3. dry with materialAfter drying with MgSO4
  4. concentrationthe organic layer was concentrated under vacuum at room temperature

出典と根拠

ORDレコード
ord-801edc6120d447d8b22eee3494dec036
出典データセット
uspto-grants-2004_12
特許番号
US06835733B2

反応ノート

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