Water → HCID 86636746, compound

HRID 385454Notes

Reaction equation

HRID 385454 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-94936ceaffbe457db850be2bc9e0096b
Source dataset
uspto-grants-2013_02
Patent number
US08367863B2

Reaction notes

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