Hydrochloric Acid → 2-Bromo-5-(4-fluorobenzyl)thiophene

HRID 52192

反応式

HRID 52192 の反応式
[Li+].CC([N-]C(C)C)C.[Br:9][C:10]1[S:11][CH:12]=[CH:13][CH:14]=1.[F:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.Cl>C1COCC1>[Br:9][C:10]1[S:11][C:12]([CH2:20][C:19]2[CH:22]=[CH:23][C:16]([F:15])=[CH:17][CH:18]=2)=[CH:13][CH:14]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 138512-BromothiopheneHCID 680214-Fluorobenzyl bromideHCID 2724682Lithium diisopropylamide

生成物 1

HCID 105400132-Bromo-5-(4-fluorobenzyl)thiophene収率 45.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a -78° C. solution of LDA (19.3 mmol) in THF was added 2-bromothiophene (3.00 g, 18.4 mmol) and the reaction mixture was stirred for 15 min. A solution of 4-fluorobenzyl bromide (3.65 g, 19.3 mmol) in THF (1 mL) was added dropwise and the reaction mixture was warmed slowly to ambient temperature and stirred for 70 hours. The reaction mixture was poured into 0.5N aqueous HCl and extracted twice with ether. The combined organic layers were washed with saturated aqueous NaHCO3 (2×) and brine, dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel (hexanes, then 3% ether/hexanes) gave 2-bromo-5-(4-fluorophenylmethyl)thiophene (2.25 g, 45%).

後処理

  1. stirringstirred for 70 hours
  2. extractionextracted twice with ether
  3. washThe combined organic layers were washed with saturated aqueous NaHCO3 (2×) and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-68dedbc32e1846dabccd5c35808bec20
出典データセット
uspto-grants-1997_04
特許番号
US05616596

関連ノート

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