10-Bromo-1-decanol

Clear yellow liquid

1, 10-Decanediol 15 (10 g, 57.47 mmol) in toluene (600 mL) was taken in a 1 L two-neck round bottom flask equipped with a Dean Stark apparatus, to which HBr (48percent, 7.15 mL, 63.21 mmol) was added and refluxed for 16 h. After cooling, the reaction mixture was washed with 1 N HCl, 2 M aq NaOH, HTo a solution of 1, 10-decandiol (3) (34.8 g, 0.2 mol, 1 equiv) in toluene (400 mL) was added 48percent HBr (22.6 mL, 0.2 mol, 1 equiv) dropwise with stirring and refluxed at 180 °C using Dean-Stark trap for 24 h. The mixture was cooled to room temperature and washed with 6 N NaOH (150 mL), 10percent HCl (150 mL), HSynthesis Example A-(1) 1, 10-Decanediol (4 g) was dissolved in 100 ml of cyclohexane, and 57percent aqueous hydrobromic acid solution (58 ml) was added to this solution. The reaction mixture was refluxed for six hours while stirring. After the reaction, the mixture was extracted three times with diethyl ether. The organic layer was neutralized with saturated sodium hydrogen carbonate solution, washed with saline solution, dried over magnesium sulfate, and filtered, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel flash chromatography (hexane: ethyl acetate = 7:3) gave 10-bromodecan-1-ol as white crystals at an 89percent yield. Molecular weight: 237.18 (CA mixture of 1, 10-decanediol (0.3 g, 1.72mmol), 48percent aq. hydrogen bromide (0.29 g, 3.58 mmol) and tetrabutylammonium iodide (0.12 g, 0.34 mmol) was subjected to MWI at 355 W for 5 min. The reaction mixture was cooled, extracted with diethyl ether (3x10 mL) and washed with saturated sodium bicarbonate solution (2 x 5 mL), 10percent aq. sodium thiosulfate (2 x 5 mL), water (2 x5 mL), and brine and dried. The evaporation of solvent under reduced pressure furnished the crude product, which was purified by column chromatography over silica gel using 5percent ethyl acetate in n-hexane to afford pure product (3, 0.32 g, 80percent) as a colourless oil.HBr (48percent in H2O, w/w, 16.3 mL, 138 mmol) was added to a mixture ofdecane-1, 10-diol (2; 20 g, 115 mmol) and toluene (250 mL). The resultingmixture was stirred at reflux temperature for 16 h. Afterreaching r.t. and careful addition of sat. aq Na2S2O3 (50 mL), the aqueouslayer was extracted with EtOAc (3 × 200 mL). The combined extractswere dried (MgSO4), filtered, and the solvent was evaporated.Purification of the residue by flash chromatography (silica gel, hexanes/EtOAc, 4:1 to 2:1) afforded the title compound as a colorless oil(19.8 g, 73percent).IR (ATR): 3328, 2924, 2853, 1463, 1437, 1371, 1352, 1256, 1242, 1129, 1055, 899, 756, 722, 644, 562, 505, 465, 445, 428, 417 cm–1.1H NMR (400 MHz, CDCl3): δ = 3.63 (t, J = 6.6 Hz, 2 H), 3.40 (t, J = 6.9Hz, 2 H), 1.88–1.80 (m, 2 H), 1.60–1.51 (m, 2 H), 1.46–1.24 (m, 13 H).13C NMR (100 MHz, CDCl3): δ = 63.2, 34.2, 32.92, 32.89, 29.6, 29.49, 29.48, 28.9, 28.3, 25.8.HRMS-ESI: m/z calcd for [C10H21BrO + Na]+: 259.0669; found:259.0668.adding toluene 500 ml in a 1 L three-necked flask, 1 175g of 10-decanediol, adding 200ml of 40percent hydrobromic acid, stirring at room temperature for 18h, separating the liquid, washing the toluene phase with 200ml saturated laboratory, drying, concentrated crude product 240g, Column chromatography (EA: PE = 4:1) gave 140 g of 10-bromofurfuryl alcohol in a yield of 59percentGeneral procedure: TMSOTf or TESOTf (2.0 equiv) was added dropwise to a solution of MOM, MEM, BOM, or SEM ether (1, 3-5) and 2, 2'-bipyridyl (3.0 equiv) in CHGeneral procedure: TMSOTf or TESOTf (2.0 equiv) was added dropwise to a solution of MOM, MEM, BOM, or SEM ether (1, 3-5) and 2, 2'-bipyridyl (3.0 equiv) in CHGeneral procedure: TMSOTf or TESOTf (2.0 equiv) was added dropwise to a solution of MOM, MEM, BOM, or SEM ether (1, 3-5) and 2, 2'-bipyridyl (3.0 equiv) in CHGeneral procedure: TMSOTf or TESOTf (2.0 equiv) was added dropwise to a solution of MOM, MEM, BOM, or SEM ether (1, 3-5) and 2, 2'-bipyridyl (3.0 equiv) in CH

Molecular Weight:237.18
XLogP3:4.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:9
Exact Mass:236.07758
Monoisotopic Mass:236.07758
Topological Polar Surface Area:20.2
Heavy Atom Count:12
Complexity:76.2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes