Dimethylformamide → HCID 58604050, compound

HRID 2113669Notes

Reaction equation

HRID 2113669 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([F:10])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][C:13]([OH:15])=O.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[Cl-].[Al+3].[Cl-].[Cl-]>C1C=CC=CC=1>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([F:10])[CH:5]=[C:4]2[C:3]=1[CH2:11][CH2:12][C:13]2=[O:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 467371922-Chloro-4-fluoro-3-methoxybenzenepropanoic acid

Product 1

HCID 58604050HCID 58604050, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 3-(2-chloro-4-fluoro-3-methoxyphenyl)propanoic acid (20.74 g, 88 mmol) in benzene (440 mL) was added DMF (0.14 mL, 1.8 mmol) followed by gradual addition of oxalyl chloride (15.4 mL, 177 mmol) during 25 minutes. After 2 hours, the reaction mixture was evaporated under vacuum to give a yellow oil. The oil was dissolved in 100 mL of benzene and evaporated under vacuum. This process was then repeated. The resulting oil was dissolved in dichloromethane (500 mL) and solid aluminum chloride (12.9 g, 96.7 mmol) was added during 5 minutes using a solid addition funnel. After 20 minutes, the reaction mixture was poured onto ca 1000 cc of ice. When most of the ice had melted, the layers were separated and the aqueous phase was extracted with dichloromethane. The combined organic layers were washed successively with 2N HCl, water and brine. After drying over sodium sulfate, the solution was evaporated under vacuum to give a yellow solid. Flash chromatography through silica gel eluting with EtOAc/hexanes/dichloromethane (10:95:95) gave 4-chloro-6-fluoro-5-methoxyindanone as a white solid.

Workup

  1. customthe reaction mixture was evaporated under vacuum
  2. customto give a yellow oil
  3. customevaporated under vacuum
  4. dissolutionThe resulting oil was dissolved in dichloromethane (500 mL)
  5. additiona solid addition funnel
  6. waitAfter 20 minutes
  7. customthe layers were separated
  8. extractionthe aqueous phase was extracted with dichloromethane
  9. washThe combined organic layers were washed successively with 2N HCl, water and brine
  10. dry with materialAfter drying over sodium sulfate
  11. customthe solution was evaporated under vacuum
  12. customto give a yellow solid

Sources & evidence

ORD record
ord-4cee90c0b79645ac84b26abef5b9fc5a
Source dataset
uspto-grants-2008_10
Patent number
US07432284B2

Reaction notes

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