Hydrochloric Acid → HCID 68553553, compound

HRID 2192743Notes

Reaction equation

HRID 2192743 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH3:13])=[C:8]([OH:14])[CH:7]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].[Br:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=1F.Cl>CN1C(=O)CCC1>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH3:13])=[C:8]([O:14][C:28]2[CH:27]=[C:26]([Cl:29])[CH:25]=[CH:24][C:23]=2[Br:22])[CH:7]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 1372751-Bromo-4-chloro-2-fluorobenzeneHCID 21079760HCID 21079760, compound

Product 1

HCID 68553553HCID 68553553, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

step 1—To a solution of ethyl 4-ethyl-3-hydroxyphenylacetate (12a, 1.000 g; 4.8 mmol) and NMP (10 mL) was added K2CO3 (1.99 g; 14.4 mmol) and 1-bromo-4-chloro-2-fluorobenzene (1.106 g; 5.28 mmol). The reaction was heated to 120° C. and monitored by TLC. After 8 h the reaction was cooled to RT and 10% HCl was added. The mixture was extracted with EtOAc and the combined extracts were washed with H2O and brine. The extracts were dried (Na2SO4) filtered and evaporated. The crude product was chromatographed with SiO2 and eluted with a gradient of hexane/EtOAc (100:0 to 60:40) to afford [3-(2-bromo-5-chloro-phenoxy)-4-ethyl-phenyl]-acetic acid ethyl ester.

Workup

  1. temperatureAfter 8 h the reaction was cooled to RT
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined extracts were washed with H2O and brine
  4. dry with materialThe extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was chromatographed with SiO2
  8. washeluted with a gradient of hexane/EtOAc (100:0 to 60:40)

Sources & evidence

ORD record
ord-bb6002ed16c14cf9a7894cf92e0b6cd4
Source dataset
uspto-grants-2012_12
Patent number
US08329755B2

Reaction notes

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