2-Fluorobenzoyl chloride → 2-Di-n-propylamino-8-(2'-fluorobenzoyl)-1,2,3,4-tetrahydronaphthalene

HRID 22140

反応式

HRID 22140 の反応式
[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8](Br)[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].C([Li])CCC.[F:24][C:25]1[CH:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27](Cl)=[O:28]>C1COCC1>[CH2:1]([N:4]([CH2:16][CH2:17][CH3:18])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([C:27](=[O:28])[C:26]3[CH:30]=[CH:31][CH:32]=[CH:33][C:25]=3[F:24])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3]

参加物

5

反応物 3

HCID 98082-Fluorobenzoyl chlorideHCID 145295648-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

生成物 1

HCID 152335372-Di-n-propylamino-8-(2'-fluorobenzoyl)-1,2,3,4-tetrahydronaphthalene収率 29.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

2-Di-n-propylamino-8-bromo-1,2,3,4-tetrahydronaphthalene (1.0 g; 3.22 mmol) dissolved in THF (25 ml) was cooled to -78° C., and 2.5 ml of n-butyllithium (1.27M in hexane) were added. After one hour, o-fluorobenzoyl chloride (0.38 ml, 3.22 mmol) was added. The mixture was stirred for 10 minutes at -78° C. after which the reaction was quenched by addition of water at -78° C. The reaction was made basic with NaOH and extracted three times with methylene chloride. The basic extract was dried (Na2SO4) and concentrated to give 2.0 g of crude residue. Purification of this material by flash silica gel chromatography using 1:1 ether:hexane containing a trace of ammonium hydroxide as solvent provided 2-di-n-propylamino-8-(2'-fluorobenzoyl)-1,2,3,4-tetrahydronaphthalene (340 mg).

後処理

  1. customwas quenched by addition of water at -78° C
  2. extractionextracted three times with methylene chloride
  3. extractionThe basic extract
  4. dry with materialwas dried (Na2SO4)
  5. concentrationconcentrated
  6. customto give 2.0 g of crude residue
  7. customPurification of this material by flash silica gel chromatography

出典と根拠

ORDレコード
ord-f1ba75c926ff440c8afffe4ef918c5b7
出典データセット
uspto-grants-1995_06
特許番号
US05426226

関連ノート

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