3-Bromobenzenemethanol

CLEAR COLOURLESS TO LIGHT YELLOW LIQUID

(3-Bromophenyl)methanolSodium borohydride (7.1 g, 186.1 mmol) in several portions was added to a solution of 3- bromobenzaldehyde (114.8 g, 620.4 mmol) in EtOH (650 mL) at 25 General procedure: Aldehyde (1 mmol) was dissolved in 10 ml ofmethanol(ethanol for ketones) and cooled to 0General procedure: In a round-bottomed flask (10 mL), equipped with a magneticstirrer bar, a solution of acetophenone (0.121 g, l mmol) was prepared in CH3CN(3 mL). To this solution, Zn(BH4)2/2NaCl (0.210 g, 1 mmol) was added. The resulting mixture was stirred at room temperature for 60 min. The reaction was monitored by TLC(eluent; Hexane/EtOAc: 10/1). After completion of the reaction, distilled water (5 mL) was added to the reaction mixture and stirred for 5 min. The mixture was extracted with CH2Cl2 (3 ×8 mL) and dried over anhydrous Na2SO4. Evaporation of the solvent followed column chromatography of the resulting crude material over silica gel (eluent; Hexane/EtOAc: 10/1) afforded crystals of 1-phenylethanol (0.l1 g, 93 percent yield, Table 2, entry 11).General procedure: In a round-bottomedflask (10 mL) charged with distilled water (5 mL), LiBHCompound 2 was prepared according to Eur. J. Org. Chem, 2002, 19, 3326-3335. In a 250 mL roundbottom was added 3-bromobenzaldehyde 1 (10.0 g, 54.0 mmol) and EtOH (25 mL). The solution was cooled to 0 °C in an ice-water bath, sodium borohydride (1.1 1 g, 29.5 mmol) was added, and the mixture was stirred at 0 °C for 1 h. Sodium sulfate decahydrate was added, and the reaction was stirred at rt for 1 h to quench the borohydride. Diethyl ether was added, and the mixture was washed with water. The organic layer was dried with sodium sulfate and concentrated under vacuum to give 2 (9.50 g, 94percent) as a clear oil. 2. General procedure: Zn(BH4)2was prepared from ZnCl4 (5.452g, 0.04 mol) and NaBH4(3.177 g, 0.084 mol)according to an available procedure in the literature11.In a round-bottomed flask (10 mL) charged withdistilled water (5 mL), Zn(BH4)2(0.095 g, 1mmol)and benzaldehyde (0.106 g, 1 mmol) was added.After fitting the flask to the external condenser atthe inside of the oven, the mixture was irradiatedwitha microwave oven (30percent power amplitude, 300 W)for60 sec. The progress of the reaction wasmonitored by TLC(eluent; CH2Cl2). At the end of thereduction, distilledwater (5 mL) was added to thereaction mixture and it wasthen extracted withCH2Cl2(2×10 mL). The combined extracts were dried over anhydrous sodium sulfate. Evaporationofthe solvent afforded the pure liquid benzyl alcohol(0.102 g, 95percent).General procedure: A 0.165 M stock solution of aldehyde or ketone (1 equiv) was prepared by dissolution in (1:1:2 IPA/H2O/NaHCO3 [1 M]). A 0.75 M stock solution of sodium dithionite (4, 5 equiv) was prepared by dissolution in (1:1:2 IPA/H2O/NaHCO3 [1 M]). The injection loops (10 mL) unless otherwise stated were primed with the two stock solutions respectively. The solutions were then pumped continuously through a 2 mL mixing chip at ambient temperature followed by a 14 mL HT Teflon coil at 110 °C (aldehydes and ketones). Unless otherwise stated the flow rate was set to 0.25 mL·min

Molecular Weight:187.03
XLogP3:2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:185.96803
Monoisotopic Mass:185.96803
Topological Polar Surface Area:20.2
Heavy Atom Count:9
Complexity:85
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes