5-Bromo-1-pentanol

Light yellow liquid

In 250mL three-necked flask add 1a (14 g, 0.135 mol), 40percent hydrobromic acid (28 mL, 0.2 mol) and 60 mL of benzene, 70 ~ 80 ° C oil bath water for 15h, TLC detection, raw material points disappear. Washed successively with 5percent sodium hydroxide solution, 10percent hydrochloric acid and saturated brine, and dried over anhydrous sodium sulfate. The crude product was separated by silica gel column chromatography (petroleum ether: ethyl acetate, V / V = 8: 1) and concentrated to give colorless to pale yellow liquid 2a (20.1g, yield 89.1percent).A round bottom flask, equipped with a Dean-Stark trap, wascharged with 1, 5-pentanediol (3.71 g, 35.6 mmol), concentratedhydrobromic acid (5 mL), and toluene (75 mL). The mixture wasstirred under refluxed for 15 h. After cooling, the reaction mixturewas extracted with 6 M sodium hydroxide (2 15 mL), 5percent HCl(2 15 mL), water (2 15 mL) and brine (20 mL). The organicswere dried over sodium sulfate and concentrated under reducedpressure to yield the title compound as an orange/brown oil(4.75 g, 2.84 mmol, 801H NMR (500 MHz, CDCl3) d 8.16(s, 1H), 7.65 (s, 1H), 7.46 (m, 6H), 7.25 (m 6H), 7.17 (m, 3H), 6.98(m, 3H), 6.48 (m, 4H), 3.59 (br, 2H), 3.11 (br, 4H), 2.65 (q, 12H, J = 7 Hz), 2.11 (br, 2H), 1.61 (m, 2H), 1.52 (m, 4H), 1.45 (m, 2H), 1.41 (s, 9H), 1.31 (m, 2H), 1.01 (t, 18H, J = 7 Hz); 13C NMR(125 MHz, CDCl3) d 180.65, 171.21, 156.78, 155.79, 155.64, 146.13, 140.35, 138.09, 130.98, 129.19, 128.54, 127.72, 126.14, 124.68, 123.33, 120.15, 113.95, 103.13, 79.37, 79.15, 70.77, 47.23, 46.91, 45.71, 44.64, 43.29, 29.65, 28.48, 28.14, 27.81, 26.53, 26.10, 24.21, 9.07; HRMS (C54H56N4O7S): calculated 904.3870, observed904.3866.

Molecular Weight:167.04
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:165.99933
Monoisotopic Mass:165.99933
Topological Polar Surface Area:20.2
Heavy Atom Count:7
Complexity:31.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes