Hydrochloric Acid → 4-Bromo-3-methoxycinnamic acid

HRID 2045702

反応式

HRID 2045702 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 580051274-Bromo-3-methoxycinnamic acid

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6342Acetonitrile溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-76d71e52e99843a7930c4130da041c17
出典データセット
uspto-grants-2013_11
特許番号
US08591878B2

関連ノート

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