Chloride → 2-(4-Fluorophenylmethyl)indene

HRID 11967

反応式

HRID 11967 の反応式
[Mg].[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]Cl)=[CH:5][CH:4]=1.[Cl-].Br[C:13]1[CH2:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2>CCOCC.Cl[Ni]1(Cl)[P](C2C=CC=CC=2)(C2C=CC=CC=2)CCC[P]1(C1C=CC=CC=1)C1C=CC=CC=1>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:13]2[CH2:21][C:20]3[C:15]([CH:14]=2)=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:5][CH:4]=1

参加物

7

反応物 4

HCID 312ChlorideHCID 96024-Fluorobenzyl chlorideHCID 5755861H-Indene, 2-bromo-HCID 5462224Magnesium

生成物 1

HCID 219769972-(4-Fluorophenylmethyl)indene

試薬・触媒・溶媒 2

HCID 178418745HCID 178418745、化合物触媒HCID 3283Diethyl Ether溶媒3 回

実験手順

To a suspension of freshly ground magnesium (0.58 g, 23 mmol) in 100 mL of ether was added about 3 mL of a 15 mL ether solution containing 3.0 g (21 mmol) of 4-fluorophenylmethyl chloride. The system was carefully heated and after initiation of the reaction, the remaining chloride solution added over 30 minutes while maintain a gentle reflux. After refluxing for 1.5 hours, the Grignard solution was cooled and cannulated to a mixture of 3.65 g (19 mmol) of 2-bromo-indene, 150 mg (0.20 mmol) of NiCl2(dppp) and 100 mL of ether. The system was gently heated to reflux overnight and then cooled and quenched by adding 150 mL of 1.0 M aqueous hydrochloric acid. The product was isolated and purified (hexanes/silica) as for 2-benzyl-indene. Yield: 3.45 g, 74 percent

後処理

  1. temperatureThe system was carefully heated
  2. customafter initiation of the reaction
  3. temperaturewhile maintain a gentle reflux
  4. temperatureAfter refluxing for 1.5 hours
  5. temperaturethe Grignard solution was cooled
  6. temperatureThe system was gently heated
  7. temperatureto reflux overnight
  8. temperaturecooled
  9. customquenched
  10. additionby adding 150 mL of 1.0 M aqueous hydrochloric acid
  11. customThe product was isolated
  12. custompurified (hexanes/silica) as for 2-benzyl-indene

出典と根拠

ORDレコード
ord-c95ea336c63e4d4ea8961bed6584d030
出典データセット
uspto-grants-2006_08
特許番号
US07098356B2

関連ノート

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