Ethyl Acetate → HCID 57995562, compound

HRID 385456Notes

Reaction equation

HRID 385456 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:15]2([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:18][CH2:17][CH2:16]2)[CH:5]=[C:6]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])[C:7]=1I.[F:24][C:25]([F:36])([F:35])[C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1.[F-].[Cs+].CCOC(C)=O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:22]([O:21][C:19]([C:15]1([C:4]2[CH:5]=[C:6]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])[C:7]([C:29]3[CH:30]=[CH:31][C:26]([C:25]([F:36])([F:35])[F:24])=[CH:27][CH:28]=3)=[C:2]([Cl:1])[CH:3]=2)[CH2:18][CH2:17][CH2:16]1)=[O:20])[CH3:23]

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 25953Cesium fluorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 57995621HCID 57995621, compound

Product 1

HCID 57995562HCID 57995562, compoundYield 25.7%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of ethyl 1-(3-chloro-4-iodo-5-(2,2,2-trifluoroethoxy)phenyl)cyclobutanecarboxylate (0.35, 7.35 mmol), 4-trifluoromethylphenylboronic acid (0.277 g, 1.47 mmol), CsF (0.277 g, 1.83 mmol) and Pd (PPh3)4 (0.084 g, 0.36 mmol) in 20 mL anhydrous 1,2-dimethoxy ethane was refluxed for 8 h under argon. The reaction mixture was cooled, and 20 mL of EtOAc and 20 mL of water were added. The organic phase was separated, dried over Na2SO4, filtered and concentrated under reduced pressure to yellow oil. The oil was purified by column chromatography over silica gel (hexane/EtOAc, 95:5) to give ethyl-1-(2-chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-4-yl)cyclobutanecarboxylate (0.182 g) as a colorless oil.

Workup

  1. temperaturewas refluxed for 8 h under argon
  2. temperatureThe reaction mixture was cooled
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure to yellow oil
  7. customThe oil was purified by column chromatography over silica gel (hexane/EtOAc, 95:5)

Sources & evidence

ORD record
ord-28d00ee75eca46bea99c499590d3799e
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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