Hydrochloric Acid → 4-Bromo-3-methoxycinnamic acid

HRID 1879273

反応式

HRID 1879273 の反応式
[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]

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

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.

後処理

  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

出典と根拠

ORDレコード
ord-30ec2bea95874b05a1ce95d501715363
出典データセット
uspto-grants-2012_11
特許番号
US08314062B2

関連ノート

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