1,7-Dibromoheptane → 1-Bromo-7-phenylheptane

HRID 1111382Notes

Reaction equation

HRID 1111382 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][Br:9].[C:10]1([Li])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[Br:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 783091,7-DibromoheptaneHCID 178506676HCID 178506676, compound

Product 1

HCID 27356031-Bromo-7-phenylheptaneYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1,7-dibromoheptane (49 g, 0.18 mol) (Aldrich) in THF (300 ml), at -30° C. to -40° C., under N2, was added, dropwise, during 3 h, a solution of phenyllithium (15 g, 0.18 mol) in cyclohexane-ether (2.0 M solution, Aldrich). The reaction was allowed to stir at -10° C. to -20° C. for 3 h and at room temperature overnight. After slow, careful dilution with H2O (50 ml), the aqueous layer was extracted with Et2O (2×150 ml). The extracts and the organic layer were combined, dried (Na2SO4) and concentrated to a yellow oil. Distillation through a Vigreaux column provided 22.5 g of 1-bromo-7-phenylheptane, bp 84°-88° C. (0.2 mm), nD24 1.5220.

Workup

  1. extractionAfter slow, careful dilution with H2O (50 ml), the aqueous layer was extracted with Et2O (2×150 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated to a yellow oil
  4. distillationDistillation through a Vigreaux column

Sources & evidence

ORD record
ord-b6b2e6b1d8e14bed88511c7e8fb48c6c
Source dataset
uspto-grants-1990_12
Patent number
US04980360

Reaction notes

Loading…