Hydrochloric Acid → 4-Bromo-3-methoxycinnamic acid

HRID 2045702

반응식

HRID 2045702 반응식
[C:1]([OH:5])(=[O:4])[CH:2]=[CH2:3].[Br:6][C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][C:8]=1[O:14][CH3:15].Cl>CC#N.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Br:6][C:7]1[CH:12]=[CH:11][C:10](/[CH:3]=[CH:2]/[C:1]([OH:5])=[O:4])=[CH:9][C:8]=1[O:14][CH3:15]

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

Acrylic acid (9.61 g, 133 mmol), TEA (37.2 mL, 267 mmol) and palladium acetate (719 mg, 3.2 mmol) were added to a solution of 1-bromo-4-iodo-2-methoxybenzene (US 2004/0254159) (33.45 g, 107 mmol) in MeCN (100 mL). The reaction mixture was heated to 90° C. for 40 min, cooled to RT and poured into 2.4 L 1M HCl. After stirring for 30 min, the solid was filtered, heated to reflux in EtOH (230 mL), allowed to cool to RT and stirred overnight. The solid was filtered and washed with 1:1 EtOH:hexanes (50 mL) to give desired product. LRMS ESI+ (M+H)+ 257.0.

후처리

  1. temperaturecooled to RT
  2. filtrationthe solid was filtered
  3. temperatureheated
  4. temperatureto reflux in EtOH (230 mL)
  5. temperatureto cool to RT
  6. stirringstirred overnight
  7. filtrationThe solid was filtered
  8. washwashed with 1:1 EtOH

출처 및 근거

ORD 기록
ord-76d71e52e99843a7930c4130da041c17
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08591878B2

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