Methanol → Bis-(2,6-dimethoxyphenyl)(methyl)phosphine
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[CH:4]=1.[Li][CH2:12][CH2:13][CH2:14][CH3:15].Cl[CH:17]([PH2:19])Cl.[CH3:20][OH:21].[CH2:22]([O:24][CH2:25]C)[CH3:23]>CN(C)CCN(C)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[P:19]([C:15]1[C:22]([O:24][CH3:25])=[CH:23][CH:12]=[CH:13][C:14]=1[O:21][CH3:20])[CH3:17]Participants
Procedure
2,6-Bis-dimethoxyphenyllithium was prepared from 14.18 g (0.103 is mole) of 1,3-dimethoxybenzene, 77 mL of a 1.6 M solution of BuLi in hexanes and 0.23 mL of N,N,N′,N′-tetramethylethylenediamine in dry diethyl ether (72 mL). Dichloromethylphosphine (5.0 g, 0.04276 mole) was added at 0° C., and the reaction mixture was stirred at room temperature overnight. Methanol (20 mL) was added, and the mixture was concentrated to about half its original volume under reduced pressure. The resulting white precipitates were filtered and were recrystallized from methanol to give white crystals of bis-(2,6-dimethoxyphenyl)(methyl)-phosphine with 48% yield (6.6 g) and melting point at 112.33° C. 1H NMR (CDCl3) δ 1.75 (s (broad), 3H, Me—P), 3.55 (s, 12H, Me—O), 6.4-7.2 (m, 6H, aromatic protons); 31P NMR (CDCl3) δ-51.5 ppm. LS/MS: found m/w is 321, calculated m/w is 321. Anal. found: C, 64.30%; H, 6.45%; calculated for C17H22O4P: C, 63.49%; H, 6.85%.
Workup
- concentrationthe mixture was concentrated to about half its original volume under reduced pressure
- customThe resulting white precipitates
- filtrationwere filtered
- customwere recrystallized from methanol
Sources & evidence
- ORD record
- ord-b0777ad8f76045ff9e345652b0d9d82f
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07998895B2
Reaction notes
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