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

HRID 52192

반응식

HRID 52192 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 105400132-Bromo-5-(4-fluorobenzyl)thiophene수율 45.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-68dedbc32e1846dabccd5c35808bec20
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616596

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