Dibromomethane → 4-Methoxydibenzofuran
Reaction equation
C(Br)Br.C1(C2C=CC=CC=2O)C=CC=CC=1.C([Si](CC)(CC)C1C2OC3C=CC=CC=3C=2C=CC=1)C.[CH3:37][O:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:40]=1[OH:51].COC1C=C(C2C=CC=CC=2O)C=CC=1>>[CH3:37][O:38][C:39]1[C:40]2[O:51][C:50]3[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=3[C:41]=2[CH:42]=[CH:43][CH:44]=1Participants
Procedure
The reaction was conducted according to the General Procedure by heating 4-MeO-dibenzofuran (8, 89 mg, 0.5 mmol, 1 equiv.), KOt-Bu (112 mg, 1 mmol, 2 equiv.) and Et3SiH (401 microliters, 2.5 mmol, 5 equiv.) in 2 ml of toluene for 20 hours at 100° C. After aqueous work up, the crude reaction mixture was purified by chromatography on silica using hexanes and hexanes-ether to recover unconsumed starting material 8 (3 mg, 0.015 mmol, 3%) and isolate dibenzofuran (1, 8.4 mg, 0.05 mmol, 10%; since fractions of 1 contained small amounts of starting 8, quantification was done by 1H-NMR with CH2Br2 as an internal standard), 1,1′-biphenyl-2-ol (2, 4.3 mg, 0.025 mmol, 5%), 4-Et3Si-dibenzofuran (3, 11 mg, 0.039 mmol, 8%), 2-methoxy-6-phenyl-phenol (9, mg, 0.025 mmol, 5%), 2-(3′-methoxyphenyl)phenol (10, 47 mg, 0.235 mmol, 47%). Note: only compounds with the yield exceeding 2% were characterized. 1H and 13C NMR spectral assignments of 9 and 10 were consistent with literature reports.
Sources & evidence
- ORD record
- ord-251217a8ed304915a95b3475f9159fd3
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309269B2
Reaction notes
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