Ethanol → 2-Chloro-4-fluorobenzyl ethyl ether

HRID 231418노트

반응식

HRID 231418 반응식
[H-].[Na+].[CH2:3]([OH:5])[CH3:4].[H][H].[Cl:8][C:9]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:10]=1[CH2:11]Br>O1CCCC1>[CH2:3]([O:5][CH2:11][C:10]1[CH:13]=[CH:14][C:15]([F:17])=[CH:16][C:9]=1[Cl:8])[CH3:4]

참가 물질

6

반응물 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 27250621-(Bromomethyl)-2-chloro-4-fluorobenzeneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 145018362-Chloro-4-fluorobenzyl ethyl ether

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Tetrahydrofuran (50 ml) was added to stirred sodium hydride (1.26 g, 0.053 mole) under a nitrogen atmosphere while being cooled in an ice-water bath. Absolute ethanol (5 ml) was then added dropwise and the reaction stirred until hydrogen evolution ceased. A solution of 2-chloro-4-fluorobenzyl bromide (10.62 g, 0.0475 mole ) in tetrahydrofuran (10 ml) was then added to the reaction mixture. The reaction mixture was allowed to stir at ambient temperature overnight. Ethanol and tetrahydrofuran were removed under reduced pressure. The reaction mixture was diluted with diethyl ether (200 ml), washed with water (4×75 ml), dried (magnesium sulfate) and concentrated under reduced pressure to remove solvent. The residue was distilled at low pressure yielding 5.27 g of 2-chloro-4-fluorobenzyl ethyl ether, b.p. 67°-68° C./10 mm Hg. The nmr spectrum was consistent with the proposed structure.

후처리

  1. temperaturewhile being cooled in an ice-water bath
  2. customEthanol and tetrahydrofuran were removed under reduced pressure
  3. additionThe reaction mixture was diluted with diethyl ether (200 ml)
  4. washwashed with water (4×75 ml)
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated under reduced pressure
  7. customto remove solvent
  8. distillationThe residue was distilled at low pressure

출처 및 근거

ORD 기록
ord-9d30306aa07d4889b9eca28842172259
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04846882

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