Methyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylate → 4-(4-tert-Butoxycarbonyl-3-fluoro-phenoxy)-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([O:16]C2C=CC(C(N3CCC3)=O)=CC=2)[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[CH:6]=1)=[O:4].[C:29]([O:33][C:34](=[O:43])[C:35]1[CH:40]=[CH:39][C:38](Br)=[CH:37][C:36]=1[F:42])([CH3:32])([CH3:31])[CH3:30].COC(C1C=C(O)C2CC(C)(C)OC=2C=1)=O>>[CH3:1][O:2][C:3]([C:5]1[CH:15]=[C:14]([O:16][C:38]2[CH:39]=[CH:40][C:35]([C:34]([O:33][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:43])=[C:36]([F:42])[CH:37]=2)[C:8]2[CH2:9][C:10]([CH3:13])([CH3:12])[O:11][C:7]=2[CH:6]=1)=[O:4]Participants
4
Reactant 3
Product 1
Procedure
The title compound was prepared in a similar manner as described for Intermediate 35b, from 4-bromo-2-fluoro-benzoic acid tert-butyl ester and 4-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester (3e). 1H NMR (400 MHz, CDCl3) δ 7.86 (t, J=8.59 Hz, 1 H) 7.25-7.31 (m, 1 H) 7.24 (s, 1 H) 6.74 (dd, J=8.84, 2.02 Hz, 1 H) 6.65 (dd, J=11.87, 2.27 Hz, 1 H) 3.88 (s, 3 H) 2.87 (s, 2 H) 1.59 (s, 9 H) 1.48 (s, 6 H); LCMS for C23H25FO6 m/z 439.00 (M+Na)+.
Sources & evidence
- ORD record
- ord-bde19c9d0e664ccfa1acc9122cb33d03
- Source dataset
- uspto-grants-2010_11
- Patent number
- US07842713B2
Reaction notes
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