Synthesis of 1,2-dibromo-1-ethoxyethane

Preparation of 1,2-dibromo-1-ethoxyethane

Dry hydrogen chloride is led cautiously into a mixture of 100 g of paraldehyde and 100 g of ethanol which is cooled in a freezing mixture. Two layers are formed, the upper of which is dried over anhydrous calcium chloride and fractionated by collecting the fraction boiling at 93-96° C (69%). To the obtained 1-chloro-2-ethoxyethane is added the theoretical quantity of bromine, portion wise (with time for decolonization in each case), with cooling in ice; hydrogen chloride is evolved. When the crude 1,2-dibromo-1-ethoxyethane product is distilled in a vacuum it has b.p. 92-95°/17 mm, the yield being 88-91%.

J. Amer. Chem. Soc, 52, 654 (1930).

0.1 mole of bromine is dropped into a stirred and ice cooled mixture of 0.1 mole of acetaldehyde and 0.1 mole of ethyl alcohol in 20 ml of benzene containing 20  g of sodium sulfate. After 20 minutes stirring at room temperature the hydrated sodium sulfate is filtered off and the filtrate is worked up by distillation in a vacuum yielding 90% of 1,2-dibromo-1-ethoxyethane, b.p. 65-68°/12 mm.

Chem. Ber., 98, 1673 (1965).

IUPAC Name

1,2-dibromo-1-ethoxyethane

InChI

InChI=1S/C4H8Br2O/c1-2-7-4(6)3-5/h4H,2-3H2,1H3

InChI Key

YNQUMIFEHUKSMO-UHFFFAOYSA-N

Canonical SMILES

CCOC(CBr)Br

Depositor-Supplied Synonyms

1,2-Dibromo-1-ethoxyethane, Ethane, 1,2-dibromo-1-ethoxy-, 2983-26-8, 105431-36-5, YNQUMIFEHUKSMO-UHFFFAOYSA-N, EINECS 221-040-7, AC1L2TU4, AC1Q24CB, 1,2-dibromo-2-ethoxyethane, 1,2-dibromo-1-ethoxy-ethane, SCHEMBL2071027, Jsp005641, Ethane,1,2-dibromo-1-ethoxy-, CTK4G3890, KST-1B2902, 1,2-bis(bromanyl)-1-ethoxy-ethane, AR-1B5704, AKOS005266801, OR056259, KB-149172, FT-0657545, V0731, A801239, S14-1491, 3B1-004060

Removed Synonyms

CID102915, 30653-58-8

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