Water → HCID 86636746, compound

HRID 1183721Notes

Reaction equation

HRID 1183721 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]([CH2:21][CH:22]2[CH2:24]C2)[C:16]([O:18][CH2:19][CH3:20])=O)[CH:5]=[C:6]([O:9][CH2:10][C:11]([F:14])([F:13])F)[C:7]=1I.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1.[F-:38].[Cs+].[CH3:40]COC(C)=O.[OH2:46]>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>[C:19]([O:18][CH:16]1[CH:21]([CH2:22][CH3:24])[CH:15]1[C:4]1[CH:5]=[C:6]([O:9][CH2:10][C:11]([F:13])([F:14])[F:38])[C:7]([C:30]2[CH:31]=[CH:32][C:27]([C:26]([F:37])([F:36])[F:25])=[CH:28][CH:29]=2)=[C:2]([Cl:1])[CH:3]=1)(=[O:46])[CH2:20][CH3:40]

Participants

8

Reactant 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 25953Cesium fluorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 57995597HCID 57995597, compound

Product 1

HCID 86636746HCID 86636746, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of ethyl 2-(3-chloro-4-iodo-5-(2,2,2-trifluoroethoxy)phenyl)-3-cyclopropylpropanoate (1.1 g, 2.4 mmol), 4-trifluoromethylphenylboronic acid (0.928 g, 4.9 mmol), CsF (0.926 g, 6.1 mmol) and Pd (PPh3)4 (0.283 g, 0.245 mmol) in 50 mL anhydrous 1,2-dimethoxy ethane was refluxed for 8 h under argon. The reaction mixture was cooled, and 40 mL of EtOAc and 40 mL of water were added. The organic phase was separated, dried over Na2SO4, filtered and concentrated under reduced pressure to give a yellow oil. The oil was purified by column chromatography over silica gel (hexane/EtOAc, 95:5) to give ethyl-2-(2-chloro-6-(2,2,2-trifluoroethoxy)-4′-(trifluoromethyl)biphenyl-4-yl)-3-cyclopropyl propanoate (0.650 g) as a yellow 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
  7. customto give a yellow oil
  8. customThe oil was purified by column chromatography over silica gel (hexane/EtOAc, 95:5)

Sources & evidence

ORD record
ord-ebd128307e6246408c4611e35ec0d277
Source dataset
uspto-grants-2014_03
Patent number
US08664249B2

Reaction notes

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