2-Bromoethyl ether

colourless liquid

21.2 g (0.2 mol) of diethylene glycol in a dry 1 L flask, 500 mL of carbon tetrachloride was added, dissolved by stirring, and cooled in an ice-water bath. 60 g (0.22 mol) of phosphorus tribromide was slowly added dropwise. The addition was complete, stirring was continued for 1 hour, the ice-water bath was removed, and the mixture was stirred at room temperature for 15 hours. Concentrate to remove the solvent. Another 500 mL of ethyl acetate was added for dissolution and then washed four times with a 5percent aqueous solution of sodium carbonate. The organic layer was dried over anhydrous sodium sulfate and concentrated to give 41.4 g of an oil (compound 11).A solution of a commercially available PEG (6.66 mmol) and triethylamine (2.32 ml, 16.65 mmol) in dry diethyl ether (10 ml) was cooled at 0° C., under a dry nitrogen atmosphere and treated dropwise with methanesulfonyl chloride (1.03 ml, 13.32 mmol). Stirring was continued for 1 h at 0° C. and at room temperature (22° C.) for 2 h. Afterwards, the diethyl ether was evaporated and dry acetone (12 ml) was added to the residue in order to precipitate most of the triethylamine hydrochloride salt, which was filtered from the solution. The filtrate, containing the dimesylate-PEG derivative was immediately treated with lithium bromide (2.31 g, 26.64 mmol) and heated to reflux for 20 h. Then the product was filtered on a small quantity of silica (3 cm) covered with celite (0.5 cm) with hexanes as the eluent. The filtrate was dried, filtered and evaporated to an oil. The α, ω-dibromo-PEG derivatives were obtained in 50 to 83percent yield. [0159] NB: Some of these α, ω-dibromo-PEG derivatives are also commercially available. [0160] 1, 5-dibromo-3-oxapentane (n=1) [0161] 50percent yield [0162] IR (NaCl, νmax, cm-1): 1279 and 1117 (C-O). [0163] 1H-NMR (CDCl3, δ ppm): 3.83 (4H, t, J=6.3 Hz, 2.x.CH2O), 3.47 (4H, t, J=6, 3 Hz, 2.x.CH2Br). [0164] 13C-NMR (CDCl3, δ ppm): 71.0 (CH2O), 30.0 (CH2Br).68.1 g of 1, 4-thioxane-1, 1-dioxo (0.5 mol), 340Gram mass of 48percent hydrobromic acid (2 moles)Was added to a 500 mL four-necked flask and mechanically stirred at 30 ° C. The gas chromatographic was followed by a 12 hour reaction.Layer, the lower layer of organic layer and then 50 ml of saturated sodium bicarbonate washing, water chestnut distillation collection 90-105 ° C boiling range, pale yellow liquid 96.7 grams, The gas content was 98.5percent and the yield was 82.1percent.A suspension of bis-(2-chloroethyl) ether (6) (5.0 g, 0.035 mol) and KBr (8.3 g, 0.07 mol) in 2:1 mixture of DMF–1, 2-dibromoethane(150 ml) was refluxed for 24 h. Saturated NaCl solution(50 ml) was then added to the reaction mixture, followedby extraction with Et2O. The solution was dried overanhydrous Na2SO4 and evaporated under vacuum, theresidue was purified by vacuum distillation at 4–5 Torr.Yield 5.25 g (65percent), dark-brown oil. NMR spectra matchedthe literature.

2,2'-dibromodiethyl ether is an important organic intermediate (building block) to synthetize substituted diethyl ether products.

Molecular Weight:231.91
XLogP3:1.6
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:4
Exact Mass:231.89214
Monoisotopic Mass:229.89419
Topological Polar Surface Area:9.2
Heavy Atom Count:7
Complexity:28.9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes