Synthesis of sec-butyl bromide

Preparation of sec-butyl bromide (2-bromobutane; butane, 2-bromo-; 2-butyl bromide; methylethylbromomethane)

Preparation of sec-butyl bromide (2-bromobutane; butane, 2-bromo-; 2-butyl bromide; methylethylbromomethane)

Preparation of sec-butyl bromide (2-bromobutane; butane, 2-bromo-; 2-butyl bromide; methylethylbromomethane)

To 250 grams of 48% hydrobromic acid contained in a 500 ml round-bottomed flask 41 ml (or 75 grams) of concentrated sulfuric acid are dropwise added. During the addition, some hydrogen bromide may be evolved. 70.4 ml (or 88 grams) of sec-butyl alcohol are added, followed by 32.5 ml (or 60 grams) of concentrated sulfuric acid in several portions with shaking, and finally a few chips of broken glass. The reaction flask is refluxed for 2-3 hours. During this period, the formation of sec-butyl bromide is almost complete and a layer of alkyl bromide separates above the acid. When the reaction is complete the flask is cooled and arranged for downward distillation. The mixture is distilled until no more oily drops of sec-butyl bromide pass over and the distillate is transferred to a separatory funnel and the lower layer containing sec-butyl bromide is removed. Crude sec-butyl bromide is washed with water, three times with an equal volume of concentrated hydrochloric acid, water, 5% sodium bicarbonate or sodium carbonate solution, and water. The sec-butyl bromide is dried with anhydrous calcium chloride or anhydrous magnesium sulfate, as completely as possible. sec-Butyl bromide is purified by distillation. The fraction passing over 90.5-92.5° C is collected yielding 150 grams of pure sec-butyl bromide.

A text book of practical organic chemistry, by A. I. Vogel, 278, 1974

IUPAC Name

2-bromobutane

InChI

InChI=1S/C4H9Br/c1-3-4(2)5/h4H,3H2,1-2H3

InChI Key

UPSXAPQYNGXVBF-UHFFFAOYSA-N

Canonical SMILES

CCC(C)Br

MeSH Synonyms

2-bromobutane, 2-bromobutane, (+-)-isomer, 2-bromobutane, (R)-isomer, 2-bromobutane, (S)-isomer, 2-bromobutane, ion(1+)

Depositor-Supplied Synonyms

2-Bromobutane, SEC-BUTYL BROMIDE, 78-76-2, Butane, 2-bromo-, 2-Butyl bromide, Methylethylbromomethane, 2-Bromo-butane, sec-Butylbromide, Secondary butyl bromide, 1-Bromo-1-methylpropane, CCRIS 106, HSDB 2197, UPSXAPQYNGXVBF-UHFFFAOYSA-N, NSC 8417, EINECS 201-140-7, SBB059931, UN2339, BRN 0505949, AI3-25262, 3-bromobutane, 2-Bromo butane, Butane,2-bromo-, sJPHAbILuP@, sec-C4H9Br, PubChem3753, 1-Methylpropyl bromide, S-BUTYL BROMIDE, AC1L1MSD, BROMOBUTANE, 2-, DSSTox_CID_1499, ACMC-209pf5, DSSTox_RID_76189, DSSTox_GSID_21499, SCHEMBL27724, (.+/-.)-2-Bromobutane, B59500_ALDRICH, KSC492I7P, AC1Q2S05, CHEMBL156276, SCHEMBL6999177, WLN: EY2&1, 19690_FLUKA, CTK3J2477, NSC8417, ATTERCOP-CHM AT113219, MolPort-001-768-736, LABOTEST-BB LTBB001155, NSC-8417, STR03634, Tox21_200633, ANW-37215, AKOS009157105, AS03110, NE10010, RP20322, RTR-037838, TRA0043476, UN 2339, CAS-78-76-2, NCGC00248774-01, NCGC00258187-01, AN-23957, KB-87231, LS-45623, SC-06798, DB-021233, TR-037838, B0561, FT-0611543, ST51046198, X5862, 2-Bromobutane [UN2339] [Flammable liquid], EN300-82118, 2-Bromobutane [UN2339] [Flammable liquid], 0-01-00-00119 (Beilstein Handbook Reference), 3B4-0639, I14-0215, 5787-31-5

Removed Synonyms

2-Bromobutane sec-Butyl bromide, CID6554

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