Iodine → 2-(4-Bromo-phenyl)-4-(2-iodo-ethyl)-5-methyl-oxazole

HRID 1445758

Reaction equation

[I:1]I.[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:18])=[C:13]([CH2:15][CH2:16]O)[N:14]=2)=[CH:6][CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CC=CC=1>C1(C)C=CC=CC=1.O.C(OCC)(=O)C>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[O:11][C:12]([CH3:18])=[C:13]([CH2:15][CH2:16][I:1])[N:14]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Add iodine (1.90 g, 7.49 mmol) to a stirred mixture of 2-[2-(4-bromo-phenyl)-5-methyl-oxazol-4-yl]-ethanol (1.503 g, 5.33 mmol), triphenylphosphine (2.101 g, 8.01 mmol), and pyridine (1.4 mL, 17 mmol) in toluene (48 mL) and heat at 100° C. for 45 min. Cool to room temperature, add ethyl acetate and water, and separate the layers. Extract the aqueous layer twice with ethyl acetate, wash the organic layer with 0.1N HCl, dry over anhydrous magnesium sulfate, and concentrate under reduced pressure. Purify the residue by flash chromatography (SiO2, elute 0% to 10% EtOAc/hexanes) to-yield 1.804 g of the title compound as a colorless solid. 1H NMR (400 MHz, CDCl3) δ 7.89 (d, J=8.4 Hz, 2H), 7.60 (d, J=8.8 Hz, 2H), 3.49 (dd, J=7.2, 7.2 Hz, 2H), 3.11 (dd, J=7.2, 7.2 Hz, 2H), 2.39 (s, 3H).

Workup

temperatureCool to room temperature
customseparate the layers
extractionExtract the aqueous layer twice with ethyl acetate
washwash the organic layer with 0.1N HCl
dry with materialdry over anhydrous magnesium sulfate
concentrationconcentrate under reduced pressure
customPurify the residue
washby flash chromatography (SiO2, elute 0% to 10% EtOAc/hexanes) to-yield 1.804 g of the title compound as a colorless solid

Sources & evidence

ORD record: ord-ceb9f050bd8e44138dbb19c5551d1f16
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666871B2

Linked notes

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