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Toluene → Triethyl(methoxymethyl)phosphonium bromide

HRID 416951
ノート
印刷プレビュー

反応式

HRID 416951 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1140TolueneHCID 27365TriethylphosphineHCID 83093Bromomethyl methyl ether

生成物 1

HCID 86623187Triethyl(methoxymethyl)phosphonium bromide収率 80%

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-38a8e166b93b40dc9b917f10363bfaf2
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08088995B2

反応ノート

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