1-(3-Methoxyphenyl)acetone → Ethyl 2-(5-bromo-3-methyl-1-(trifluoromethylsulfonyl-oxy)naphthalen-2-yl)-2-(4-methoxybenzyloxy)acetate
Reaction equation
CO[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9]([O:13][S:14]([C:17]([F:20])([F:19])[F:18])(=[O:16])=[O:15])=[C:8]([CH:21]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:7]([CH3:37])=[CH:6]2.[Br:38]C1C=CC=CC=1CC(=O)C.COC1C=C(CC(=O)C)C=CC=1>>[Br:38][C:4]1[CH:3]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH:6]=[C:7]([CH3:37])[C:8]([CH:21]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:9]2[O:13][S:14]([C:17]([F:18])([F:20])[F:19])(=[O:15])=[O:16]Participants
4
Reactant 3
Product 1
Procedure
Ethyl 2-(5-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-(4-methoxybenzyl oxy)acetate (35) was prepared similarly to ethyl 2-(6-methoxy-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-(4-methoxybenzyloxy)acetate of Example 32, using 1-(2-bromophenyl)propan-2-one as the starting material instead of 1-(3-methoxyphenyl)propan-2-one. 1H-NMR: 400 MHz, (CDCl3) δ: 8.11 (s, 1H), 8.01 (d, J=8.8 Hz, 1H), 7.85 (d, J=7.6 Hz, 1H), 7.40 (t, J=7.6 Hz, 1H), 7.23 (d, J=8.4 Hz, 2H), 6.81 (d, J=7.6 Hz, 2H), 5.61 (s, 1H), 4.62 (q, J=11.2 Hz, 2H), 4.26-4.15 (m, 2H), 3.75 (s, 3H), 2.62 (s, 3H), 1.18 (t, J=6.8 Hz, 3H).
Sources & evidence
- ORD record
- ord-f589472a0b7248c5b4e05617e0efa0cc
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09102614B2
Reaction notes
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