Hydrochloric Acid → 4-Bromo-3-methoxycinnamic acid

HRID 1879273

반응식

HRID 1879273 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][C:3]=1[O:9][CH3:10].[C:11]([OH:15])(=[O:14])[CH:12]=[CH2:13].Cl>CC#N.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:13]=[CH:12]/[C:11]([OH:15])=[O:14])=[CH:4][C:3]=1[O:9][CH3:10]

참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 6581Acrylic AcidHCID 121872021-Bromo-4-iodo-2-methoxybenzene

생성물 1

HCID 580051274-Bromo-3-methoxycinnamic acid

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6342Acetonitrile용매

반응 조건

온도
90 °C

실험 절차

To a solution of 1-bromo-4-iodo-2-methoxybenzene (L. A. Hasvold et al., US 2004/0254159) in MeCN (1.1 M) was added acrylic acid (1.24 eq.), TEA (2.5 eq.) and palladium acetate (0.03 eq). The reaction mixture was heated to 90° C. for 40 min, cooled to RT and poured into 1N HCl. After sting for 30 min, the solid was filtered, heated to reflux in EtOH (2.3 M), allowed to cool to RT and stirred overnight. The solid was filtered and washed with 1:1 EtOH:hexane to give the desired product 119. LRMS ESI+ (M+H)+ 257.0.

후처리

  1. temperaturecooled to RT
  2. filtrationthe solid was filtered
  3. temperatureheated
  4. temperatureto reflux in EtOH (2.3 M)
  5. temperatureto cool to RT
  6. filtrationThe solid was filtered
  7. washwashed with 1:1 EtOH

출처 및 근거

ORD 기록
ord-30ec2bea95874b05a1ce95d501715363
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08314062B2

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