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Toluene → Triethyl(methoxymethyl)phosphonium bromide

HRID 416951
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HRID 416951 반응식
[Br:1][CH2:2][O:3][CH3:4].C1(C)C=CC=CC=1.[CH2:12]([P:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH3:13]>CCCCCC>[Br-:1].[CH2:12]([P+:14]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:2][O:3][CH3:4])[CH3:13]
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참가 물질

5

반응물 3

HCID 1140TolueneHCID 27365TriethylphosphineHCID 83093Bromomethyl methyl ether

생성물 1

HCID 86623187Triethyl(methoxymethyl)phosphonium bromide수율 80%

시약·촉매·용매 1

HCID 8058Hexane용매

실험 절차

62 g (0.5 moles) of bromomethylmethyl ether (a reagent available from Tokyo Chemical Industry Co., Ltd.) was added dropwise in 236 g (0.5 moles) of a 25% toluene solution of triethylphosphine (HISHICOLIN (registered trademark) P-2, a trade name of Nippon Chemical Industrial Co., Ltd.), and the mixture was allowed to react at 70 to 80° C. for 6 hours. After completion of the reaction, hexane was added for crystallization, thereby obtaining 97 g (percent yield: 80%) of a crystal of triethyl(methoxymethyl)phosphonium bromide. 86 g (0.3 moles) of lithium bis(trifluoromethylsulfonyl)imide (a reagent available from Kanto Chemical Co., Inc.) was added to 73 g (0.3 moles) of this triethyl(methoxymethyl)phosphonium bromide, and the mixture was allowed to react in an aqueous system. Subsequently, the reaction mixture was stirred for aging at room temperature for 3 hours. After completion of stirring, a lower layer (product) was separated. The separated product was washed with pure water four times and then washed with hexane four times. After completion of washing, the product was dried in vacuo at 100° C. and at a degree of vacuum of 0.5 kPa for 5 hours. Confirmation of the obtained product was carried out by means of 1H-NMR, 13C-NMR, 31P-NMR and 19F-NMR. A yield of the product (colorless transparent liquid) was 104 g (percent yield: 78%), and it was confirmed by 3P-NMR that its purity was 98% or more.

후처리

  1. customto react at 70 to 80° C. for 6 hours
  2. additionwas added for crystallization

출처 및 근거

ORD 기록
ord-38a8e166b93b40dc9b917f10363bfaf2
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08088995B2

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