Dichloromethane → Ethyl 2-(2-chlorophenyl)-1,3-thiazole-4-carboxylate

HRID 1823945Notes

Reaction equation

HRID 1823945 reaction equation
Br[C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>C(OCCOCC)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[C:2]1[S:3][CH:4]=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylateHCID 27343222-Chlorophenylboronic acid

Product 1

HCID 15170575Ethyl 2-(2-chlorophenyl)-1,3-thiazole-4-carboxylateYield 63.3%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 12375Ethylene glycol diethyl etherSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 2-bromo-4-thiazolecarboxylate (2.0 g, 8.5 mmol), prepared as described above, in ethylene glycol diethyl ether (15 mL) is added 2-chlorophenylboronic acid (1.73 g, 11.1 mmol), 2N sodium carbonate (17 mL) and tetrakis(triphenylphosphine) palladium (0) (492 mg, 0.43 mmol). The reaction is subsequently sealed and heated to 80° C. for 3 hours under an argon atmosphere. Once complete, the reaction mixture is poured into CH2Cl2 and of water is added. The organic layer is separated, dried over sodium sulfate and concentrated to provide a yellow oil. The crude product is purified by column chromatography (10% ethyl acetate in hexanes) to afford 1.44 g of ethyl 2-(2-chlorophenyl)-4-thiazolecarboxylate.

Workup

  1. customThe reaction is subsequently sealed
  2. additionis added
  3. customThe organic layer is separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customto provide a yellow oil
  7. customThe crude product is purified by column chromatography (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-3b45b0bba10549c69377ef080ddd42e4
Source dataset
uspto-grants-2006_05
Patent number
US07041690B2

Reaction notes

Loading…