Cesium fluoride → tert-Butyl {[5-chloro-4'-(ethylthio)biphenyl-2-yl]oxy}acetate

HRID 1694681Notes

Reaction equation

HRID 1694681 reaction equation
[C:1]([O:5][C:6](=[O:17])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1Br)([CH3:4])([CH3:3])[CH3:2].[CH2:18]([S:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)[CH3:19].[F-].[Cs+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:17])=[C:10]([C:24]2[CH:25]=[CH:26][C:21]([S:20][CH2:18][CH3:19])=[CH:22][CH:23]=2)[CH:11]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 27343534-Ethylthiophenylboronic acidHCID 49766393tert-Butyl (2-bromo-4-chlorophenoxy)acetate

Product 1

HCID 86609213tert-Butyl {[5-chloro-4'-(ethylthio)biphenyl-2-yl]oxy}acetate

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of the product from step (i) (2 g), 4-(ethylthio)phenylboronic acid (1.5 g), cesium fluoride (2 g) and Pd(dppf)Cl2 (0.2 g) in dioxane (40 ml) was heated under reflux for 3 h. After cooling the mixture was partitioned between diethylether and water. The organics were separated, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 5% EtOAc/iso-hexane. Yield 0.92 g

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 h
  3. temperatureAfter cooling the mixture
  4. customwas partitioned between diethylether and water
  5. customThe organics were separated
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe residue was purified by chromatography on silica eluting with 5% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-36dcfc905ad84df7a82bcd2c69093e50
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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