Benzyl Bromide → HCID 11006844, compound

HRID 1721495Notes

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[C:6]1([C:12]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[N:13][CH2:14][P:15]([CH2:20][N:21]=[C:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:19])[O:16][CH2:17][CH3:18])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH2:41](Br)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.[CH3:49][CH2:50][CH2:51]CCC>C1COCC1.CCOCC>[C:29]1([C:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[N:21][CH:20]([P:15]([CH:14]([N:13]=[C:12]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)(=[O:19])[O:16][CH2:17][CH3:18])[CH2:4][C:3]2[CH:51]=[CH:50][CH:49]=[CH:1][CH:2]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

Conditions

Temperature: -70 °C

Procedure

A 1.53 N butyllithium solution (3.0 ml; 4.59 mmol) in hexane is added dropwise to a stirred solution of ethyl phosphinate 3 (1000 mg; 2.08 mmol) in THF (35 ml) at -78° C. under an atmosphere of argon. After 10 minutes benzyl bromide (1.00 ml; 8.42 mmol) is added dropwise to the deep-red reaction solution. After 70 hours stirring at -70° C. the reaction solution is diluted with ether and extracted with saturated aqueous ammonium chloride solution. The organic phase is dried over Na2SO4 and evaporated under reduced pressure. The bis-alkylated phosphinates 5 (1303 mg, 95% of theory) are obtained after purification on silica gel using column chromatography (ethyl acetate/heptane=2/3).

Workup

extractionextracted with saturated aqueous ammonium chloride solution
dry with materialThe organic phase is dried over Na2SO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-b85f8aa3070547068f02f865ae96c7c4
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05510504

Reaction notes

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