Hydrochloric Acid → 4-Methyldibenzofuran-3-carboxaldehyde

HRID 964567Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][C:6]=2[C:14]=1[CH3:15].C([Li])CCC.Cl.[K+].[Br-].C[CH2:25][O:26]CC>CN(C=O)C>[CH3:15][C:14]1[C:6]2[O:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:5]=2[CH:4]=[CH:3][C:2]=1[CH:25]=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

3-Bromo4-methyldibenzofuran (26.11 g, 0.1 mol) suspended in dry ether (700 ml) was cooled to 0° C. and n-butyl lithium (1.6M in hexane, 62.5 ml, 0.1 mol) was added and the reaction stirred for 5 mins. DMF (5 ml) in ether (12 ml) was added and the reaction heated to reflux for 1 hour. The mixture was poured onto a mixture of conc. HCl (25 ml) and ice (1 l). The organic phase was separated and the aqueous extreacted with ether. The combined organic phases were dried (MgSO4) and evaporated in vacuo. The resulting solid was crystallised from IMS to give off-white needles which were dried at 60° C. under vacuum (4.68 g, 22%). Further product could be obtained from the mother liquor. (Found: C, 78.97; H, 4.56. C14H10O2 0.15H2O requires: C, 78.97; H, 4.88%); δH [2H6 ]-DMSO 10.4 (1H, s, CHO), (8.2 (1H, d), 8.15 (1H, d), 7.9 (1H, d), 7.8 (1H, d), 7.65 (1H, t), 7.45 (1H, t), 2.85 (3H, s); m/z 210 (M+); νmax (KBr disc)/cm-1 1686.

Workup

temperaturethe reaction heated
temperatureto reflux for 1 hour
customThe organic phase was separated
dry with materialThe combined organic phases were dried (MgSO4)
customevaporated in vacuo
customThe resulting solid was crystallised from IMS
customto give off-white needles which
customwere dried at 60° C. under vacuum (4.68 g, 22%)
customFurther product could be obtained from the mother liquor

Sources & evidence

ORD record: ord-4b5f37f853f34ff99c0d2bc65c56c954
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05770598

Reaction notes

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