1-Chloro-4-(chloromethyl)benzene → 4-(2-Fluoroethoxy)benzyl 4-chlorobenzyl ether

HRID 1583592노트

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HRID 1583592 반응식
[F:1][CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][OH:10])=[CH:7][CH:6]=1.[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18]Cl)=[CH:16][CH:15]=1.[OH-].[Na+]>[Br-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[Cl:13][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][O:10][CH2:9][C:8]2[CH:11]=[CH:12][C:5]([O:4][CH2:3][CH2:2][F:1])=[CH:6][CH:7]=2)=[CH:16][CH:15]=1

참가 물질

6

반응물 3

HCID 77231-Chloro-4-(chloromethyl)benzeneHCID 14798Sodium HydroxideHCID 13367643(4-(2-Fluoroethoxy)phenyl)methanol

생성물 1

HCID 133676524-(2-Fluoroethoxy)benzyl 4-chlorobenzyl ether수율 89.6%

시약·촉매·용매 2

HCID 165294Benzyltriethylammonium bromide촉매HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

A mixture consisting of 5.3 g of 4-(2-fluoroethoxy)benzyl alcohol, 5.0 g of 4-chlorobenzyl chloride, 0.5 g of triethylbenzylammonium bromide and 20 g of a 50% aqueous solution of sodium hydroxide was stirred at 50° C. for 4 hours. The reaction mixture was cooled to room temperature, poured into water, and extracted with toluene. The toluene layer was washed with water, and dried over anhydrous sodium sulfate. Toluene was evaporated under reduced pressure. The resulting crude ether was purified by silica gel (200 g) column chromatography (developing solvent: benzene) to give 8.2 g of the desired 4-(2-fluoroethoxy)benzyl 4-chlorobenzyl ether as pale yellow crystals.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with toluene
  3. washThe toluene layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customToluene was evaporated under reduced pressure
  6. customThe resulting crude ether was purified by silica gel (200 g) column chromatography (developing solvent: benzene)

출처 및 근거

ORD 기록
ord-ebbb4618413245ad80423353649d1525
출처 데이터셋
uspto-grants-1985_11
특허 번호
US04552894

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