Triethylamine → 5-Chloro-2-(2-chlorophenyl)-7-(3-hydroxy-1-butynyl)-benzoxazole

HRID 842100Notes

Reaction equation

HRID 842100 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])=[N:7][C:6]=2[CH:5]=[C:4]([Cl:18])[CH:3]=1.[CH3:19][CH:20]([OH:23])[C:21]#[CH:22].C(N(CC)CC)C>C1(C)C=CC=CC=1.[Cu]I>[Cl:18][C:4]1[CH:3]=[C:2]([C:22]#[C:21][CH:20]([OH:23])[CH3:19])[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:17])=[N:7][C:6]=2[CH:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 162393-Butyn-2-olHCID 46392547-Bromo-5-chloro-2-(2-chlorophenyl)-1,3-benzoxazole

Product 1

HCID 46392555-Chloro-2-(2-chlorophenyl)-7-(3-hydroxy-1-butynyl)-benzoxazole

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolvent

Procedure

15.98 g (46.6 mmol) of 7-bromo-5-chloro-2-(2-chlorophenyl)-benzoxazole and 5 5.48 ml (69.9 mmol) of (±)-3-butyn-2-ol were heated for 6 h at 90-5° C. in 47 ml of toluene with 47 ml of triethylamine, 163.5 mg (233 μmol) of bis-triphenylphosphine-palladium(II)-dichloride and 8.9 mg (46.6 23 μmol) of copper(I) iodide. The reaction was filtered and the solid washed with toluene. The filtrate was evaporated in vacuo to dryness, the residue taken up in 150 ml of dichloromethane, extracted twice with 50 ml of 1 N HCl, dried with sodium sulfate, and filtered through 120 g of silica gel in a column. The title compound (11.11 g) was recovered as an off-white solid. A recrystallized sample from di-isopropyl ether had mp 129-31° C.

Workup

  1. filtrationThe reaction was filtered
  2. washthe solid washed with toluene
  3. customThe filtrate was evaporated in vacuo to dryness
  4. extractionextracted twice with 50 ml of 1 N HCl
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered through 120 g of silica gel in a column
  7. customThe title compound (11.11 g) was recovered as an off-white solid

Sources & evidence

ORD record
ord-67031ac3d51842e2b56c7159d7e2d5c1
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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