Toluene → HCID 86627974, compound
Reaction equation
[Br:1][CH2:2][CH2:3][O:4][CH3:5].C1(C)C=CC=CC=1.[CH2:13]([P:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:14]>CCCCCC>[Br-:1].[CH2:13]([P+:15]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:2][CH2:3][O:4][CH3:5])[CH3:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
73 g (0.5 moles) of 2-bromoethylmethyl 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 125 g (percent yield: 97%) of a crystal of triethyl(2-methoxyethyl) phosphonium bromide. 33 g (0.3 moles) of sodium borofluoride (a reagent available from Kanto Chemical Co., Inc.) was added to 77 g (0.3 moles) of this triethyl (2-methoxyethyl)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 product was completely dehydrated at 100° C. and at a degree of vacuum of 0.5 kPa, to which was further added 100 mL of dry methylene chloride, and a precipitate was filtered. This filtrate was concentrated and dried in vacuo at 100° C. and at a degree of vacuum of 0.5 kPa for 5 hours. Confirmation of the thus 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 60 g (percent yield: 76%), and it was confirmed by 31P-NMR that its purity was 98% or more.
Workup
- customto react at 70 to 80° C. for 6 hours
- additionwas added for crystallization
Sources & evidence
- ORD record
- ord-93030cb666ee4261838e3383a536a669
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08088995B2
Reaction notes
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