Carbon tetrabromide → 1-Bromo-5-(2-methoxyethoxy)methoxypentane

HRID 974699노트

반응식

HRID 974699 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]O.C(Br)(Br)(Br)[Br:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:15][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1]

참가 물질

5

반응물 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 15097256HCID 15097256, 화합물

생성물 1

HCID 150972571-Bromo-5-(2-methoxyethoxy)methoxypentane수율 90.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 48.40 g of 5-(2-methoxyethoxy)methoxy-1-pentanol (prepared as described in Preparation 39) and 100.19 g of carbon tetrabromide dissolved in 500 ml of methylene chloride was added 79.32 g of triphenylphosphine, whilst ice-cooling (at 5° to 8° C.). The mixture was stirred at room temperature for one hour, after which the solvent was removed by evaporation under reduced pressure. Diethyl ether was then added. The insoluble materials were filtered off and the filtrate was concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through 850 g of silica gel and 57.87 g of the title compound were obtained from the fractions eluted with a 1:9 by volume mixture of ethyl acetate and hexane, as a colorless oil.

후처리

  1. temperaturewhilst ice-cooling (at 5° to 8° C.)
  2. customafter which the solvent was removed by evaporation under reduced pressure
  3. additionDiethyl ether was then added
  4. filtrationThe insoluble materials were filtered off
  5. concentrationthe filtrate was concentrated by evaporation under reduced pressure

출처 및 근거

ORD 기록
ord-501a845839da46e38f26767b314cd7e4
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05068340

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