Hydrochloric Acid → 4-Bromo-3-methoxycinnamic acid

HRID 1095292

反応式

HRID 1095292 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].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]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 6581Acrylic AcidHCID 8471TriethylamineHCID 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, 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.

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 hexane (50 mL)

出典と根拠

ORDレコード
ord-2fa9947f028c4ade94fef91a49981a77
出典データセット
uspto-grants-2012_03
特許番号
US08138164B2

関連ノート

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