Sodium Hydroxide → 7-Bromo-1,2,3,4-tetrahydronaphthalen-1-one

HRID 1517025ノート

反応式

HRID 1517025 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:4][CH:3]=1.[OH-].[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][CH2:9][CH2:10][C:11]2=[O:13])=[CH:6][CH:7]=1

参加物

3

反応物 2

HCID 14798Sodium HydroxideHCID 2527324-(4-Bromophenyl)butyric Acid

生成物 1

HCID 2527317-Bromo-1,2,3,4-tetrahydronaphthalen-1-one収率 55%

反応条件

温度
90 °C

実験手順

The product from Step B (97 g, 397 mmol) was added to polyphosphoric acid (580 g) and the resulting mixture was stirred at 90° C. for 10 minutes. After cooling to 0° C., 6 M NaOH (2 l) was added and the mixture was extracted with methyl tert-butyl ether. The organic extracts were dried over magnesium sulfate to give 7-bromo-3,4-dihydronaphthalen-1-one (49 g, 55%) after:chromatography (6:1 to 4:1 heptane/ethyl acetate) and recrystallization from cyclohexane: 1H NMR (300 MHz, DMSO-d6) δ 7.91 (d, J=2.1 Hz, 1H), 7.71 (dd, J=8.1, 2.1 Hz, 1H), 7.34 (d, J=8.1 Hz, 1H), 2.90 (t, J=6.0 Hz, 2H), 2.61 (t, J=6.3 Hz, 2H), 1.99-2.07 (m, 2H).

後処理

  1. temperatureAfter cooling to 0° C.
  2. extractionthe mixture was extracted with methyl tert-butyl ether
  3. dry with materialThe organic extracts were dried over magnesium sulfate

出典と根拠

ORDレコード
ord-4f3d6e36fdc747399ef0cf59a4ea6b60
出典データセット
uspto-grants-2012_07
特許番号
US08227486B2

反応ノート

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