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

HRID 1929327Notes

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 triphenylphosphine (0.71 g, 2.7 mmol) under argon with stirring. The mixture was heated at 100° C. for 20 hours 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 a 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) δ1.96 (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 a 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-b9ff31b68b5342b1a21b7d449693b7d4
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188064B2

Reaction notes

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