Acetic Acid → HCID 357762, compound

HRID 1647366Notes

Reaction equation

HRID 1647366 reaction equation
[CH2:1]1[O:14][C:7]([C:8]2[CH:13]=[CH:12][CH:11]=CC=2)=[C:3]([C:4](O)=O)[O:2]1.[Br:15]Br.[Na].[C:18]([OH:21])(=[O:20])[CH3:19]>O>[CH2:1]1[O:14][C:7]2[CH:8]=[CH:13][C:12]([CH2:11][CH:19]([Br:15])[C:18]([OH:21])=[O:20])=[CH:4][C:3]=2[O:2]1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 24408BromineHCID 5360545SodiumHCID 54131645HCID 54131645, compound

Product 1

HCID 357762HCID 357762, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Stir powdered methylenedioxy cinnamic acid (19.2g, 210mmol) in glacial acetic acid (200mL) at room temperature while adding a solution of bromine (16g, 100mol) in acetic acid (50mL) over 30 minutes. Stir the homogeneous yellow solution for 15 minutes and add a solution of sodium cyabiborohydride (20g) in water (50mL) over 30 minutes. Stir for 48 hours at room temperature. Add water (70mL) and stir for an additional 2 hours. Filter and wash the filtercake with acetic acid/water. Evaporate the solvent in vacuo and partition the residue between chloroform and water. Dry the organic phase (MgSO4) and evaporate the solvent in vacuo. Redissolve the residue in chloroform, filter and evaporate the solvent in vacuo to give 3-(3,4-methylenedioxyphenyl)-2-bromopropionic acid as a crystalline solid (15.1g).

Workup

  1. stirringStir for 48 hours at room temperature
  2. filtrationFilter
  3. washwash the filtercake with acetic acid/water
  4. customEvaporate the solvent in vacuo
  5. custompartition the residue between chloroform and water
  6. dry with materialDry the organic phase (MgSO4)
  7. customevaporate the solvent in vacuo
  8. dissolutionRedissolve the residue in chloroform
  9. filtrationfilter
  10. customevaporate the solvent in vacuo

Sources & evidence

ORD record
ord-ca3372de784c4efc85adc55256b36ca0
Source dataset
uspto-grants-1995_07
Patent number
US05430145

Reaction notes

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