Iodine → 2-(4-Bromo-2-chlorophenyl)-1,3-oxazole

HRID 394856Notes

Reaction equation

HRID 394856 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([NH:8][CH2:9][CH:10]=[O:11])=O)=[C:4]([Cl:14])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.C(N(CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]2[O:11][CH:10]=[CH:9][N:8]=2)=[C:4]([Cl:14])[CH:3]=1

Participants

6

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 223137814-Bromo-2-chloro-N-(2-oxoethyl)benzamide

Product 1

HCID 223137822-(4-Bromo-2-chlorophenyl)-1,3-oxazoleYield 20%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-bromo-2-chloro-N-(2-oxoethyl)benzamide (1.00 g, 3.617 mmol) in CH2Cl2 (30 mL) were added triphenylphosphine (1.90 g, 7.234 mmol), iodine (1.84 g, 7.234 mmol) and triethylamine (2.0 mL, 14.47 mmol) at room temperature. After 24 hour, the mixture was washed with water (20 mL), dried over MgSO4. Removal of the solvent, gave an oily recidue, which was purified by flash chromatography eluting with ethyl acetate/hexane (1/5) to give title compound (0.185 g, 20% yield).

Workup

  1. washthe mixture was washed with water (20 mL)
  2. dry with materialdried over MgSO4
  3. customRemoval of the solvent
  4. customgave an oily recidue, which
  5. customwas purified by flash chromatography
  6. washeluting with ethyl acetate/hexane (1/5)

Sources & evidence

ORD record
ord-28f5235f7fd94425bacb3390a13fa483
Source dataset
uspto-grants-2003_08
Patent number
US06603008B1

Reaction notes

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