Triethylamine → 3-Chloro-1,2-benzoxazole

HRID 746819Notes

Reaction equation

HRID 746819 reaction equation
O[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1.C(N(CC)CC)C.P(Cl)(Cl)([Cl:20])=O>CCOCC>[Cl:20][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178518983HCID 178518983, compound

Product 1

HCID 27797803-Chloro-1,2-benzoxazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2-Hydroxy benzisoxazole 11 (1.03 gr, 6.25 mmol), triethylarnine (632 mg, 6.25 mmol) and phosphorousoxychloride (1.92 gr, 12.5 mmol) were heated in a sealed tube at 150° C. for 18 h. After this time the reaction was cooled to room temperature and diluted with ether and carefully quenched with excess ice/water. The resulting mixture was stirred for 15 min then the organic layer was washed with water (2×), brine (1×), dried with magnesium sulfate, filtered and evaporated to afford 12 as a white solid after column chromatography (hexanes/ethyl acetate, 97:3); 1H-NMR (CDCl3, 500 MHz) δ 7.65-7.63 9 m, 2H), 7.42 (dd, 1H).

Workup

  1. customcarefully quenched with excess ice/water
  2. washthe organic layer was washed with water (2×), brine (1×)
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-36b00af80d4d46ab9b72786ea6395a97
Source dataset
uspto-grants-2008_07
Patent number
US07393960B2

Reaction notes

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