Phosphoric Acid → Ethyl 6-chloro-1-benzofuran-7-carboxylate
Reaction equation
NC1C2OC=CC=2C=C(F)C=1.[CH2:12]([C:15]1[C:16]([OH:27])=[C:17]([C:23]([Cl:26])=[CH:24][CH:25]=1)[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:13]=C.O=[O+][O-].ClC1C=CC(CC=O)=C(O)C=1C(OCC)=O.P(=O)(O)(O)O>>[Cl:26][C:23]1[CH:24]=[CH:25][C:15]2[CH:12]=[CH:13][O:27][C:16]=2[C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19]Participants
6
Procedure
Using analogous procedures to those described in the third paragraph of the portion of Note [6] in Example 2 that is concerned with the preparation of 7-amino-5-fluorobenzofuran, ethyl 3-allyl-6-chloro-2-hydroxybenzoate was reacted with ozone and the resultant product, 2-(4-chloro-3-ethoxycarbonyl-2-hydroxyphenyl)acetaldehyde, was treated with 85% phosphoric acid to give ethyl 6-chlorobenzofuran-7-carboxylate (5.9 g); NMR Spectrum: (DMSOd6) 1.35 (t, 3H), 4.45 (q, 2H), 7.10 (d, 1H), 7.45 (d, 1H), 7.85 (d, 1H), 8.15 (d, 1H).
Sources & evidence
- ORD record
- ord-5e17a5c2e9b5474f8a4a0b21fc722075
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06849625B2
Reaction notes
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