Hydrochloric Acid → 4-Bromo-3-methoxycinnamic acid

HRID 2045702

Reaction equation

HRID 2045702 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

HCID 580051274-Bromo-3-methoxycinnamic acid

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-76d71e52e99843a7930c4130da041c17
Source dataset
uspto-grants-2013_11
Patent number
US08591878B2

Linked notes

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