Triethylamine → 7-Methyl-5-nitro-1-benzofuran

HRID 1162043Notes

Reaction equation

I[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[CH3:14]C1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[Sn](C)(C)(C)C.CCN(CC)CC>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:14][C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

7-Iodo-5-nitro-benzofuran (6.5 g, 22.1 mmol), Pd(OAc)2 (1 g, 3.9 mmol), P(o-tolyl)3, Me4Sn, Et3N were dissolved in DMF (40 mL) and portioned out in 13 tubes and heated at 100° C. for 10 min each using controlled microwave energy. The reaction mixtures were combined and filtered and the solvent was evaporated. The crude material was purified using flash chromatography (using a gradient of isohexane—10% EtOAc in isohexane). Yield: 2.82 g (70%) of 7-methyl-5-nitro-1-benzofuran. 1H NMR (400 MHz, CDCl3) δ ppm 2.51-2.64 (m, 3H) 6.90 (d, J=2.3 Hz, 1H) 7.77 (d, J=2.3 Hz, 1H) 8.04 (d, J=1.3 Hz, 1H) 8.37 (d, J=2.3 Hz, 1H); HPLC 96% Rt=2.31 min (System A; 10-97% in 3 min ACE column). MS (ESI+) for C9H7NO3 m/z 178 (M+H)+.

Workup

customThe reaction mixtures
filtrationfiltered
customthe solvent was evaporated
customThe crude material was purified

Sources & evidence

ORD record: ord-92f4f4fa5f4249c7a8d8ab9a5f4ca864
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820675B2

Reaction notes

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