Potassium Chloride → Tert-butyl 2-(4-(thiazol-2-yl)phenoxy)acetate

HRID 1191956Notes

Reaction equation

HRID 1191956 reaction equation
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.CC1(C)C(C)(C)OB([C:15]2[CH:29]=[CH:28][C:18]([O:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[CH:17][CH:16]=2)O1.[Cl-].[K+].C([O-])([O-])=O.[Na+].[Na+]>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.CCO.C1(C)C=CC=CC=1>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[C:15]1[CH:29]=[CH:28][C:18]([O:19][CH2:20][C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 4873Potassium ChlorideHCID 10340Sodium CarbonateHCID 764302-BromothiazoleHCID 59852411Tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetate

Product 1

HCID 86691024Tert-butyl 2-(4-(thiazol-2-yl)phenoxy)acetateYield 95%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-bromothiazole (265 μL, 2.97 mmol), tert-butyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)acetate (1.19 g, 3.56 mmol), KCl (664.7 mg, 8.91 mmol) in a 4:1 mixture of toluene (20 mL)/EtOH (5 mL) was added an aqueous solution of Na2CO3 2M (11.8 mL). The flask was evacuated and re-filled with nitrogen three times and then, tetrakis(triphenylphosphine)palladium (0) (346.2 mg, 0.30 mmol) was added. The reaction mixture was heated to 100° C. for 4 h. When the reaction was completed, inorganic solids were removed by filtration through Celite® and washing with several portions of dichloromethane, then the solvent was evaporated. The residue was absorbed onto silica then subjected to flash chromatography (SiO2, hexane: ethyl acetate (AcOEt), 9:1) to afford 825.2 mg of de tert-butyl 2-(4-(thiazol-2-yl)phenoxy)acetate as a white solid (95% yield). RMN1H (CDCl3, 400 MHz): δ 7.95-7.86; (m, 2H), 7.81; (d, J=3.3 Hz, 1H), 6.99-6.85; (m, 1H), 4.57; (s, 2H), 1.49; (s, 1H) ppm.

Workup

  1. customThe flask was evacuated
  2. additionre-filled with nitrogen three times
  3. custominorganic solids were removed by filtration through Celite®
  4. washwashing with several portions of dichloromethane
  5. customthe solvent was evaporated
  6. customThe residue was absorbed onto silica

Sources & evidence

ORD record
ord-15fcc509425b4f889b56bbe397f11f0b
Source dataset
uspto-grants-2014_03
Patent number
US08680126B2

Reaction notes

Loading…