2-(4-Bromophenyl)ethanol

CLEAR COLOURLESS TO LIGHT YELLOW LIQUID

5.5a (6 g, 26.2 mmol, 1.0equiv) was dissolved in THE (100 mL) and cooled toO °C. LiBH4 (2M in THE) (1.41 g, 52.4 mmol, 2.0 equiv) was added drop wise at 0 °C and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with water and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate and concentrated to afford product 5.5b (4.5 g, 85.5 percent yield). LCMS (mlz): 204.8 [M+H]. 1H NMR (400 MHz, DMSO) 6 7.56 — 7.35 (m, 2H), 7.27 — 7.07 (m, 2H), 4.67 (t, J = 5.2 Hz, 1 H), 3.58 (td, J = 6.8, 5.4 Hz, 2H), 2.69 (t, J = 6.9 Hz, 2H).The solution of 1, 4-dibromobenzene (40 g, 0.17 mol) in drydiethyl ether (200 mL) was cooled to 40 C and n-buthyllithium(105.6 mL, 1.6 M in hexanes, 0.17 mol) was added dropwise for1 h. The mixture was allowed to warm up to rt and stirred for2 h. The reaction was once again cooled to 40 C and a solutionof ethylene epoxide (8.46 mL, 0.17 mol) in 40 mL of diethyl etherwas added slowly to the mixture. The reaction mixture was slowlywarmed to room temperature and stirred for 1 h at room temperature.Then 40 mL of NH4Cl was added to quench the reaction. Theproduct was extracted with diethyl ether (3 100 mL). Theorganic layers were dried over MgSO4, filtered and concentrated.Distillation afforded 28.63 g (85percent) of a colourless liquid of 10.4-r2-(2-Bromoethoxy)ethvnbenzonitrile(T) 2-(4-BromophenvDethanol To a chilled solution (about OThe specific operation is as follows: The bromophenylacetic acid was added to 200ml of tetrahydrofuran, Stirring cooled to 0 ° C after adding lithium aluminum hydride in batches, the end of the addition, After the reaction was heated to 25 ~ 30 ° C for 2h, 300ml of water and 400ml of dichloromethane were separated, The organic phase was added to 20g of anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure at 30-35 ° C.Obtained light yellow oil (brominated S1-1): 18.7g, under ice bath, To bromine S1-1 was added dropwise phosphorus tribromide, dropping temperature during the control at 0 ~ 10 , Dropping is completed, incubated 10min insulation, a white smoke generated, stirring, warming to 75 ~ 80 , After stirring for 2h, 30ml of saturated sodium bicarbonate solution, 200ml of ethyl acetate, Stirring 20min liquid separation, the organic phase 40 ~ 45 filtrate was concentrated under reduced pressure, A yellow liquid (bromination S2) was obtained: 22.1 g. Yield: 90.0percent.General procedure: Phenethyl alcohol (3a) A two neck Schlenk flask equipped with a magnetic stirring bar and septum was heated with heat gun (~400 °C) for 10 min under high vacuum. After cooling to room temperature, the flask was flushed with argon (3 times). Zn-dust (654 mg, 2.0 equiv, 10.0 mmol) was added followed by THF (20 mL). 1, 2-Dibromoethane (5 molpercent) was added and the reaction mixture was heated until ebullition occurs. After cooling to rt, chlorotrimethylsilane (1 molpercent) was added and the mixture was heated again till ebullition occurs. The flask was again cooled to rt and benzyl chloride (633 mg, 5.0 mmol, 1 equiv) was added as a solution in THF (10 mL) and it was heated at 70 °C for 2 h and cooled to rt. Paraformaldehyde (450 mg, 3.0 equiv. 15.0 mmol) was slowly added at rt and the flask was again heated at 70 °C for 6 h. The solution was cooled to rt and saturated NH

Molecular Weight:201.06
XLogP3:1.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:199.98368
Monoisotopic Mass:199.98368
Topological Polar Surface Area:20.2
Heavy Atom Count:10
Complexity:87.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes