ChemicalBook CAS DataBase List Butyldi-1-adamantylphosphine

Butyldi-1-adamantylphosphine synthesis

6synthesis methods

Product Name:Butyldi-1-adamantylphosphine
CAS Number:321921-71-5
Molecular formula:C24H39P
Molecular Weight:358.54

Phosphonium salt (2.2 mmol) was added to a cooled solution (- 78 °C) of Et3N (4.44 g, 44 mmol) in di-n-butyl ether (20 mL). The reaction mixture was stirred at -78 °C for 5 h and then allowed to warm gradually to r.t. The solvent was removed under vacuum and the residue was dissolved in degassed EtOH (5 mL). After stirring for 15 min, the solid was filtered off and dried to yield the desired phosphine, which can be further purified by crystallization from EtOH. Butyldi-1-adamantylphosphine, yield 90%.
31P NMR (C6D6)δ: 24.9. Mp 108-110°C. IR (KBr): 3425 (m, br), 2952 (s), 2847 (s), 2847 (s), 2675 (w), 1446 cm-1 (m). 1H NMR (250 MHz, C6D6): δ = 0.96 (3 H, t, 3JH, H = 7.3 Hz, CH3), 1.35-2.03 (36 H, m, adamantyl-30H, butyl-6H). 13C NMR (62 MHz, C6D6): δ = 41.3 (d, 2JC,P = 11.3 Hz, C-2), 37.4 (C-4), 36.1 (d, 1JC,P = 23.5 Hz, C-1), 33.9 (d, 1JC,P = 26.2 Hz, butyl-α -CH2), 29.1 (d, 3JC,P = 7.6 Hz, C-3), 24.9 (d, 2JC,P = 13.1 Hz, butyl-β -CH2), 17.1 (d, 3JC,P = 21.6 Hz, butyl-γ -CH2), 14.3 (butyl-CH3). MS (EI, 70 eV): m/z (%) = 358 (M+, 60), 135 (Ad+, 100).

109-65-9 Synthesis

109-65-9
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131211-27-3 Synthesis

131211-27-3
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321921-71-5
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$9.00/250mg

Yield:321921-71-5 4.6 g (13 mmol, 85%)

Reaction Conditions:

with n-butyllithium in toluene;

Steps:

1 Example 1

4.6 g (15 mmol) of di(1-adamantyl)phosphine were placed in 50 ml of di-n-butyl ether, and 20 ml of a 2.5 M solution of n-BuLi in toluene (50 mmol) were added. The mixture was refluxed for 1 h and cooled and 4.1 g (30 mmol) of 1-butyl bromide were added dropwise. The mixture was refluxed for 30 min, cooled and washed with saturated ammonium chloride solution (3*), the organic phase was separated off and dried over sodium sulfate and the solvent was distilled off under reduced pressure. Yield: 4.6 g (13 mmol, 85%) of di(1-adamantyl)-n-butylphosphine. The product can be recrystallized from di-n-butyl ether (m.p.: 102° C.). ³¹P{¹H} NMR (162.0 MHz, C₆D₆, 297 K): δ=24.6

References:

US2004/68131,2004,A1

157282-19-4 Synthesis