Hydrochloric Acid → 4-Bromo-3-methoxycinnamic acid

HRID 1095292

반응식

HRID 1095292 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].CCN(CC)CC.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

7

반응물 4

HCID 313Hydrochloric AcidHCID 6581Acrylic AcidHCID 8471TriethylamineHCID 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, EXAMPLE 57B) (33.45 g, 107 mmol) in MeCN (100 mL) was added acrylic acid (9.61 g, 133 mmol), Et3N (37.2 mL, 267 mmol) and palladium acetate (719 mg, 3.2 mmol). The reaction mixture was heated to 90° C. for 40 minutes, cooled to RT and poured into 2.4 L 1M HCl. After stirring for 30 minutes, 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 hexane (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 hexane (50 mL)

출처 및 근거

ORD 기록
ord-2fa9947f028c4ade94fef91a49981a77
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138164B2

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