Hydrogen Bromide → methyl (E)-3-(4-bromo-2,6-dichlorophenyl)acrylate

HRID 337192

반응식

HRID 337192 반응식
[Br:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:5](N)=[C:4]([Cl:10])[CH:3]=1.Br.N([O-])=O.[Na+].[C:16]([O:20][CH3:21])(=[O:19])[CH:17]=[CH2:18]>CC(C)=O.O>[Br:1][C:2]1[CH:8]=[C:7]([Cl:9])[C:5](/[CH:18]=[CH:17]/[C:16]([O:20][CH3:21])=[O:19])=[C:4]([Cl:10])[CH:3]=1

참가 물질

7

반응물 4

HCID 260Hydrogen BromideHCID 7294Methyl AcrylateHCID 696804-Bromo-2,6-dichloroanilineHCID 23668193Sodium Nitrite

생성물 1

HCID 86646793methyl (E)-3-(4-bromo-2,6-dichlorophenyl)acrylate

시약·촉매·용매 2

HCID 180Acetone용매HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

4-Bromo-2,6-dichloroaniline (5, 80 g) was dissolved in acetone (640 mL), and a 48% hydrogen bromide aqueous solution (120 mL) was added, followed by stirring at 0° C. A sodium nitrite (32 g) aqueous solution (160 ml,) was added dropwise thereto, the mixture was stirred for 30 minutes, and methyl acrylate (200 nit), and water (200 mL) were added, followed by stirring for 1 hour. At room temperature, cuprous oxide (2 g) was added, followed by stirring for 2 hours. The reaction solution was extracted with ethyl acetate, and purified by column chromatography to obtain methyl (E)-3-(4-bromo-2,6-dichlorophenyl)acrylate (48.5 g). Methyl (E)-3-(4-bromo-2,6-dichlorophenyl)acrylate (48.5 g) was dissolved in dichloromethane, an ozone gas was introduced at −70° C., and ozone oxidization was performed. To the reaction solution was added dimethyl sulfide (40 mL), and this was extracted with ethyl acetate to obtain 4-bromo-2,6-dichlorobenzaldehyde (6, 37.2 g).

후처리

  1. stirringthe mixture was stirred for 30 minutes
  2. stirringby stirring for 1 hour
  3. stirringby stirring for 2 hours
  4. extractionThe reaction solution was extracted with ethyl acetate
  5. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-461827c04cd24ae0a2de80cddea142a2
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889722B2

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