Synthesis of cyclopentyl bromide

Preparation of cyclopentyl bromide

Alternative Names: bromocyclopentane; cyclopentylbromide; cyclopentane, bromo-;

Preparation of cyclopentyl bromide (bromocyclopentane; cyclopentylbromide; cyclopentane, bromo-)

Preparation of cyclopentyl bromide (bromocyclopentane; cyclopentylbromide; cyclopentane, bromo-)

43 grams of cyclopentanol are mixed with 176 ml (or 260 grams) of 48% hydrobromic acid in a 500 ml distilling flask, fitted with an efficient condenser and a receiver. The flask is gently heated and the cyclopentyl bromide is slowly distilled (few drops per second) until about half of the liquid has passed over. The lower cyclopentyl bromide layer is separated. The obtained crude cyclopentyl bromide is washed with an equal volume of concentrated hydrochloric acid in order to remove unreacted cyclopentanol, then with water, 5% sodium bicarbonate solution, water, and dried with anhydrous calcium chloride. Cyclopentyl bromide is purified by distillation. The fraction passing over 135-137° C is collected yielding 55 grams of pure cyclopentyl bromide.

A text book of practical organic chemistry, by A. I. Vogel, 277, 1974

IUPAC Name

bromocyclopentane

InChI

InChI=1S/C5H9Br/c6-5-3-1-2-4-5/h5H,1-4H2

InChI Key

BRTFVKHPEHKBQF-UHFFFAOYSA-N

Canonical SMILES

C1CCC(C1)Br

Depositor-Supplied Synonyms

Bromocyclopentane, CYCLOPENTYL BROMIDE, cyclopentylbromide, 137-43-9, Cyclopentane, bromo-, bromo cyclopentane, bromo-cyclopentane, BRTFVKHPEHKBQF-UHFFFAOYSA-N, SBB040823, bromocyclopentan, NSC1110, cyclopentyl-bromide, sFpHAbILimUP@, 4-bromocyclopentane, 1-bromo-cyclopentane, ACMC-209ccm, AC1L1RL1, AC1Q26CS, AC1Q26CT, SCHEMBL70317, KSC177Q9T, C115207_ALDRICH, Jsp002265, CTK0H7899, MolPort-000-153-781, EBD54304, NSC 1110, NSC-1110, STR00677, EINECS 205-294-6, ANW-20276, AR-1I0793, ZINC01587858, AKOS000121495, MCULE-9383923023, RP21245, RTC-020986, TRA0018829, AJ-27639, AK-44525, AN-43800, BR-44525, CJ-05579, CJ-25387, KB-76293, SC-22609, AI3-23448, ST2412765, TC-020986, AM20080273, B1006, FT-0600015, ST50214403, M-5891, 49556-EP2280001A1, 49556-EP2295414A1, 49556-EP2295432A1, 49556-EP2298767A1, 49556-EP2311840A1, 128909-EP2274983A1, 128909-EP2286811A1, 128909-EP2295429A1, 3B4-2658, I14-0256, InChI=1/C5H9Br/c6-5-3-1-2-4-5/h5H,1-4H

Removed Synonyms

CID8728, 13891-87-7

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