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

HRID 974699ノート

反応式

HRID 974699 の反応式
[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]

参加物

5

反応物 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 15097256HCID 15097256、化合物

生成物 1

HCID 150972571-Bromo-5-(2-methoxyethoxy)methoxypentane収率 90.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-501a845839da46e38f26767b314cd7e4
出典データセット
uspto-grants-1991_11
特許番号
US05068340

反応ノート

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