1-Propanol, 3-bromo-, 1-acetate

To a stirred solution of 3-hromopropan-.1-oi (8.0 g, 57.55 mmoi) in dry DCM (40 mL), Et3N (12.OmL, 86.32 mmol) was added and stirred at room temperature for 1() mm. After thai Ac20 (6.5 mL, 69.06 mmoi) in DCM (5 mL) was added drop wise 0 °C and stirred at room temperature for 16 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with IN HC1 solution and extracted with I)CM. The combined organic layer were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography using 1 0percent EtOAc/hexane to atrd X.10475] Yield: 10.0 g, 96percent; ‘H NMR (400 MHz, CDC13) δ 4.1 9-4.1 7 (m, 2H), 3.47 (t, ./ 6.5 Hz, 2H), 2.21-2.18 (m, 2H), 2.06 (s, 3H).To a stirred solution of l-bromo-3-propanol 147 (8.0 g, 57.55 mmol) in dry DCM (40 mL) was added Et3N (12.0 mL, 86.32 mmol) and stirred at room temperature for 10 min. After that acetic anhydride (6.5 mL, 69.06 mmol) in DCM (5 mL) was added dropwise at 0 °C and stirred at room temperature for 16h. Progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with IN HCl solution and extracted with DCM. Combined organic layer was washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. The crude product was purified by column chromatography using 10percent EtOAc in hexane to afford 148. Yield: 10 g, 96percent; NMR: 1H NMR (400 MHz, Chloroform-d3) δ 4.19 - 4.17 (m, 2H), 3.47 (t, J= 6.5 Hz, 2H), 2.19 (m, 2H), 2.06 (d, J= 3.4 Hz, 3H).3-Bromopropanol 4-1 (3.22 g, 23.2 mmol) was mixed with 2.36 g (23.2 mmol) acetic anhydride and 4.73 g (46.6 mmol) of triethylamine in methylene chloride and stirred overnight at room temperature. The resulting solution was washed with 1 M HCl, and the organic layer was removed to afford 3.8 g (90percent) of the product acetate 4-2 as a yellow oil.3-Bromopropanol was dissolved in dichloromethane (150 mL) at room temperature, triethylamine (14.5 g, 14.4 mmol) was added successively, Acetic anhydride (14.7 g, 14.4 mmol), followed by reaction at room temperature for 12 hours. The organic phase was adjusted to pH 7 with 0.5 mol / L dilute hydrochloric acid solution (20 mL), the organic phase was separated and the organic phase was saturated with a saturated aqueous solution of sodium bicarbonate (100 mL) Brine solution (100 mL x 1), dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated to dryness to give yellow liquid intermediate 9 (11.4 g, yield 87.percent).Preparation 8 Preparation 8

Molecular Weight:180.02
XLogP3:1.8
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:178.97077
Monoisotopic Mass:178.97077
Topological Polar Surface Area:40.1
Heavy Atom Count:8
Formal Charge:-1
Complexity:67.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes