N-bromobutanimide → Methyl (E)-4-(Bromomethyl)cinnamate

HRID 1105630노트

반응식

HRID 1105630 반응식
[C:1](/[CH:5]=[CH:6]/[C:7]1[CH:12]=[CH:11][C:10]([CH3:13])=[CH:9][CH:8]=1)([O:3][CH3:4])=[O:2].[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[C:1](/[CH:5]=[CH:6]/[C:7]1[CH:8]=[CH:9][C:10]([CH2:13][Br:14])=[CH:11][CH:12]=1)([O:3][CH3:4])=[O:2]

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 5314312Methyl (2E)-3-(4-methylphenyl)-2-propenoate

생성물 1

HCID 11658908Methyl (E)-4-(Bromomethyl)cinnamate수율 99.3%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

실험 절차

A mixture of 4-{(E)-2-carbomethoxyethenyl}toluene (17.6 g), N-bromosuccinimide (17.8 g) and a trace of dibenzoxylperoxide was refluxed in carbon tetrachloride under illumination until the brown-red colour disappeared. Filtration and evaporation of the solvent gave 4-{(E)-2-carbomethoxyethenyl}benzyl bromide (25.3 g). This was dissolved in dry tetrahydrofuran, heated with the sodium salt of ethyl acetoacetate (15.2 g) and a trace of potassium iodide and refluxed for 1.5 days. The solvent was removed the residue partitioned between ether and water and the ether layer dried. Removal of the solvent gave an oil (26.6 g). This was stirred with sodium hydroxide (10 g) in water (400 ml) for 2 days. The solution was extracted with ether, the aqueous layer made acidic with hydrochloric acid and this was heated on a steam bath for 1 h. The solution was extracted with chloroform and the organic layer dried (MgSO4). Removal of the solvent gave the acid of the title compound (11.0 g). This was esterified with methanol-sulphuric acid to give the title compound. τ(CDCl3) 7.9 (3H, s), 7.0-7.5 (4H, m), 6.25 (3H, s), 3.65 (1H, d, J= 16 Hz), 2.85 (2H, d, J=8 Hz), 2.6 (2H, d, J=8 Hz), 2.4 (1H, d, J=16 Hz).

후처리

  1. filtrationFiltration and evaporation of the solvent

출처 및 근거

ORD 기록
ord-0ba4495ca4184f1db81cd711e292195b
출처 데이터셋
uspto-grants-1982_01
특허 번호
US04309443

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