Acetic Acid → 3-Bromo-5-(3-pyridylmethyl)benzaldehyde

HRID 2210060Notes

Reaction equation

C([Li])(CC)C.Br[C:7]1[CH:8]=[C:9]([CH:17]=[C:18]([Br:20])[CH:19]=1)[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.CN(C)[CH:23]=[O:24].C(O)(=O)C>CCCCCC.CCOCC.O>[Br:20][C:18]1[CH:19]=[C:7]([CH:8]=[C:9]([CH2:10][C:11]2[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:17]=1)[CH:23]=[O:24]

Participants

Conditions

Temperature: -78 °C

Procedure

A 1.3M solution of s-butyllithium in hexane (27.7 ml) was added dropwise to a stirred suspension of 3-(3,5-dibromobenzyl)pyridine (Preparation 3; 9.81 g) in dry ether (300 ml) at -78° C. under an atmosphere of dry nitrogen. The resulting mixture was stirred at -78° C. for 15 minutes and then N,N-dimethylformamide (6.60 g) was added dropwise. This mixture was stirred at -78° C. for a further 30 minutes, allowed to warm to -20° C. and the glacial acetic acid (12 ml) was added. After 10 minutes, water (150 ml) was added and the organic phase separated. The aqueous layer was washed with ethyl acetate, then the combined organic solutions washed with saturated aqueous sodium bicarbonate solution and dried (MgSO4). Evaporation under vacuum of the solvent gave a solid which was crystallised from ether-hexane to give the title compound (5.25 g), m.p. 97°-98° C. Found: C,56.21; H,3.71; N,5.19. C13H10BrNO requires C,56.54; H,3.65; N,5.07%.

Workup

stirringThis mixture was stirred at -78° C. for a further 30 minutes
temperatureto warm to -20° C.
waitAfter 10 minutes
customthe organic phase separated
washThe aqueous layer was washed with ethyl acetate
washthe combined organic solutions washed with saturated aqueous sodium bicarbonate solution
dry with materialdried (MgSO4)
customEvaporation under vacuum of the solvent
customgave a solid which
customwas crystallised from ether-hexane

Sources & evidence

ORD record: ord-223b6999537a4c57a4b3420dc934e81c
Source dataset: uspto-grants-1995_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05457118

Reaction notes

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