Triphenylphosphine → Phosphonium, [3-(methoxymethoxy)propyl]triphenyl-, bromide

HRID 491339

Reaction equation

[Br:1][CH2:2][CH2:3][CH2:4][O:5][CH2:6][O:7][CH3:8].[C:9]1([P:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[Br-:1].[CH3:8][O:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][P+:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 1-bromo-3-(methoxymethoxy)propane (0.46 g, 2.5 mmol) in anhydrous toluene (1.5 mL) was added triphenylphoshine (0.71 g, 2.7 mmol) under argon with stirring. The mixture was heated at 100° C. for 20 h and cooled to room temperature. The liquid was decanted and the solid residue was grounded with spatula, filtered and washed several times with ether. After drying overnight in vacuum dessicator colorless crystals of phosphonium salt A (0.98 g, 88%) could be used in the Wittig reaction without further purification. A: 1H NMR (500 MHz, CDCl3) δ 1.96 (2H, m, CH2—CH2—CH2), 3.31 (3H, s, O—CH3), 3.85 (2H, br t, J=5.6 Hz, CH2—CH2—O), 4.00 (2H, m, P—CH2), 4.60 (2H, s, O—CH2—O), 7.70, 7.79 and 7.86 (6H, 3H and 6H, each m, Ar—H); Anal. Calcd for C23H26O2PBr: C, 62.03, H, 5.88, Br, 17.94. Found: C, 61.87, H, 5.77, Br, 17.89.

Workup

temperaturecooled to room temperature
customThe liquid was decanted
filtrationfiltered
washwashed several times with ether
dry with materialAfter drying overnight in vacuum dessicator colorless crystals of phosphonium salt A (0.98 g, 88%)
customcould be used in the Wittig reaction without further purification

Sources & evidence

ORD record: ord-e750918d95f54791b57ec57a9dc3a01c
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531527B2

Linked notes

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