Dimethyl Sulfoxide → Ethyl 4-[4-(difluoromethyl)phenoxy]-2-formyl-1-benzofuran-6-carboxylate
Reaction equation
Br[CH2:2][C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=[C:8]([O:17][C:18]3[CH:23]=[CH:22][C:21]([CH:24]([F:26])[F:25])=[CH:20][CH:19]=3)[C:6]=2[CH:7]=1.CS(C)=[O:29]>>[F:25][CH:24]([F:26])[C:21]1[CH:22]=[CH:23][C:18]([O:17][C:8]2[C:6]3[CH:7]=[C:3]([CH:2]=[O:29])[O:4][C:5]=3[CH:11]=[C:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:9]=2)=[CH:19][CH:20]=1Participants
Procedure
A solution of ethyl 2-(bromomethyl)-4-[4-(difluoromethyl)phenoxy]-1-benzofuran-6-carboxylate (440 mg, 1.03 mmol) and IBX (579 mg, 2.07 mmol) in DMSO (2 mL) was heated at 65° C. for 3 h. The reaction was quenched with water and the product was extracted with CHCl3 (3×). The combined organic layers was washed with water (2×), dried over MgSO4 and concentrated. The product was purified via gradient silica gel chromatography using hexanes/EtOAc (100/0 to 50/50) to give the title compound (300 mg, 81%) as a white solid. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 1.39 (t, J=7.16 Hz, 3 H) 4.39 (q, J=7.16 Hz, 2 H) 6.67 (t, J=56.42 Hz, 1 H) 7.11-7.18 (m, J=8.67 Hz, 2 H) 7.48 (d, J=0.94 Hz, 1 H) 7.51 (d, J=0.94 Hz, 1H) 7.55 (d, J=8.67 Hz, 2 H) 8.08 (d, J=0.94 Hz, 1 H) 9.87 (s, 1 H).
Workup
- customThe reaction was quenched with water
- extractionthe product was extracted with CHCl3 (3×)
- washThe combined organic layers was washed with water (2×)
- dry with materialdried over MgSO4
- concentrationconcentrated
- customThe product was purified via gradient silica gel chromatography
Sources & evidence
- ORD record
- ord-f97285afda2c4a06b0b2f7c508bd50d4
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842713B2
Reaction notes
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