Potassium Carbonate → HCID 5020942, compound

HRID 1468160Notes

Reaction equation

HRID 1468160 reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]([OH:16])=O)=[CH:9][CH:8]=1.[C:17]([O-])([O-])=[O:18].[K+].[K+].[OH-].[Na+]>CN(C=O)C>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13](=[CH:14][OH:16])[CH:17]=[O:18])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 74654Benzeneacetic acid, 4-bromo-

Product 1

HCID 5020942HCID 5020942, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
75 °C

Procedure

Cool to 4° C. phosphorous oxychloride (2.34 mL, 26.0 mmol) in a 100 mL flask. To this, add 5 mL of DMF and stir mixture for 5 min. Remove the flask from the cooling bath and heat at 75° C. Add (4-bromophenyl)acetic acid (2.00 g, 9.30 mmol) in one portion with an additional 5 mL of DMF and stir the mixture at 75° C. under Ar for 16 h. Pour the mixture into ice and neutralize by slow addition of K2CO3. Heat the solution at 75° C. and make strongly basic by the addition of 50% aq. NaOH resulting in an oil. Extract the oil from the aq. phase with 2×70 mL of CH2Cl2, dry with MgSO4, filter and concentrate to give 2.10 g, 99% of 2-(4-bromo-phenyl)-3-hydroxy-propenal.

Workup

  1. customRemove the flask from the cooling bath
  2. additionPour the mixture into ice and neutralize
  3. temperatureHeat the solution at 75° C.
  4. extractionExtract the oil from the aq. phase with 2×70 mL of CH2Cl2
  5. dry with materialdry with MgSO4
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-02957d82b4ee4577809f565be6d75b4a
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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