Acetic Acid → HCID 357762, compound

HRID 260332Notes

Reaction equation

HRID 260332 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 (19.2 g, 210 mmol) in glacial acetic acid (200 mL) at room temperature while adding a solution of bromine (16 g, 100 mmol) in acetic acid (50 mL) over 30 minutes. Stir the homogeneous yellow solution for 15 minutes and add a solution of sodium cyabiborohydride (20 g) in water (50 mL) over 30 minutes. Stir for 48 hours at room temperature. Add water (70 mL) 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 (15.1 g).

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-b03d9b6f39144cada85bc3bee5f89850
Source dataset
uspto-grants-1996_06
Patent number
US05527795

Reaction notes

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