Benzyl Bromide → HCID 11197766, compound

To a stirred solution containing 2.00 g (8.96 mmol) of 9-bromo-1-nonanol in 20 mL of anhydrous THF were added 1.55 mL (12.60 mmol) of benzyl bromide followed by 677 mg (16.94 mmol) of a 60% suspension of NaH in mineral oil. The reaction mixture was stirred overnight under argon atmosphere at room temperature. The reaction mixture was carefully quenched with saturated aqueous sodium bicarbonate. The mixture was poured into 100 nit of water and extracted with two portions of 100 mL of ether. The combined organic solution was washed with a portion of 100 mL of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with hexanes and then with hexanes-ethyl acetate 4:1 gave the expected product as colorless oil: yield 2.54 g (90%). 1H-NMR (CDCl3) δ 7.86 (m, 5H), 4.51 (s, 2H), 3.47 (t, 2H, J=6.4), 3.40 (t, 2H, J=6.8), 1.85 (m, 2H), 1.62 (m, 2H), 1.39 (m, 10H); 13C-NMR (CDCl3) δ 138.70, 128.34, 127.62, 127.47, 72.86, 70.46, 34.02, 32.83, 29.76, 29.38, 29.36, 28.71, 28.15, 28.16

1. customThe reaction mixture was carefully quenched with saturated aqueous sodium bicarbonate
2. additionThe mixture was poured into 100 nit of water
3. extractionextracted with two portions of 100 mL of ether
4. washThe combined organic solution was washed with a portion of 100 mL of brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated under diminished pressure
7. customThe residue was purified by chromatography on a silica gel column
8. washElution with hexanes

ORD record

ord-0feedeca13d44cc88a97d14c92965451

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08952025B2