Triphenylphosphine → Tert-butyl 2-(4-(5-(4-chlorophenyl)thiazol-2-yl)phenoxy)acetate

HRID 1191957Notes

Reaction equation

HRID 1191957 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:20]=[CH:19][C:9]([O:10][CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:8][CH:7]=1.[Cl:21][C:22]1[CH:27]=[CH:26][C:25](I)=[CH:24][CH:23]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(#N)C>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:5]2[S:1][C:2]([C:6]3[CH:7]=[CH:8][C:9]([O:10][CH2:11][C:12]([O:14][C:15]([CH3:17])([CH3:16])[CH3:18])=[O:13])=[CH:19][CH:20]=3)=[N:3][CH:4]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 125101-Chloro-4-iodobenzeneHCID 86691024Tert-butyl 2-(4-(thiazol-2-yl)phenoxy)acetate

Product 1

HCID 86691025Tert-butyl 2-(4-(5-(4-chlorophenyl)thiazol-2-yl)phenoxy)acetateYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 2-(4-(thiazol-2-yl)phenoxy)acetate (360 mg, 1.23 mmol) and 1-chloro-4-iodobenzene (412.5 mg, 1.73 mmol) in anhydrous acetonitrile (ACN) (5.2 mL) was added PPh3 (32.74 mg, 124 μmol) and Ag2CO3 (685.2 mg, 2.46 mmol). The flask was evacuated and re-filled with nitrogen three times and then PdCl2dppf was added (50.5 mg, 0.062 mmol). The reaction mixture was heated under Ar atmosphere for 72 h at 60° C. When the reaction was completed, the reaction mixture was filtered through Celite® (inorganic solids were removed) and the precipitate was washed with several portions of dichloromethane(3×20 mL). The filtrate was evaporated, and the residue was absorbed onto silica then subjected to flash chromatography (SiO2, hexane: ethyl acetate (AcOEt), 9:1) to afford 322.5 mg of tert-butyl 2-(4-(5-(4-chlorophenyl)thiazol-2-yl)phenoxy)acetate as a yellow solid (76% yield). RMN1H (CDCl3, 400 MHz): δ 7.94; (s, 1H), 7.92-7.87; (m, 2H), 7.56-7.46; (m, 2H), 7.42-7.35; (m, 2H), 7.01-6.93; (m, 2H), 4.57; (d, J=3.6 Hz, 2H), 1.50; (s, 9H) ppm.

Workup

  1. customThe flask was evacuated
  2. additionre-filled with nitrogen three times
  3. additionPdCl2dppf was added (50.5 mg, 0.062 mmol)
  4. filtrationthe reaction mixture was filtered through Celite® (inorganic solids were removed)
  5. washthe precipitate was washed with several portions of dichloromethane(3×20 mL)
  6. customThe filtrate was evaporated
  7. customthe residue was absorbed onto silica

Sources & evidence

ORD record
ord-108986afe4f04188848eddd324ebc964
Source dataset
uspto-grants-2014_03
Patent number
US08680126B2

Reaction notes

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