Triphenylphosphine → 4-Vinylbenzyl bromide

Temperature

0 °C

Bromine (16.4 g, 103 mmol) was slowly added to a solution of triphenylphosphine (28.87 g, 110.1 mmol) in CH2Cl2 (260 mL) at 0° C. After 10 minutes, 4-vinylbenzyl alcohol (12.5 g, 93.3 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h. The reaction mixture was washed with water (1×) followed by brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was triturated with petroleum ether (3×), and the ethereal solution was concentrated in vacuo. The residue was purified by flash chromatography (hexanes) to afford 4-vinyl-benzyl bromide (6.23 g). 1H NMR (400 MHz, CDCl3) δ 7.32-7.45 (m, 4H), 6.72 (dd, 1H), 5.77 (d, 1H), 5.28 (d, 1H), 4.50 (s, 2H).

1. washThe reaction mixture was washed with water (1×)
2. dry with materialThe organic solution was dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customThe product was triturated with petroleum ether (3×)
6. concentrationthe ethereal solution was concentrated in vacuo
7. customThe residue was purified by flash chromatography (hexanes)

ORD record

ord-273b0c41b0f74ee6b876a8018eb33328

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06492412B2