Ethyl 2-tert-butoxy-2-(7-chloro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate → Ethyl 2-(7-chloro-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetate

HRID 514153Notes

Reaction equation

HRID 514153 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)C(OS(C(F)(F)F)(=O)=O)=C(C(=O)C([O-])=O)C(C)=C2.C([O:31][CH:32]([C:38]1[C:47]([CH3:48])=[CH:46][C:45]2[C:40](=[CH:41][C:42]([Cl:49])=[CH:43][CH:44]=2)[C:39]=1OS(C(F)(F)F)(=O)=O)[C:33]([O:35][CH2:36][CH3:37])=[O:34])(C)(C)C>>[Cl:49][C:42]1[CH:41]=[C:40]2[C:45]([CH:46]=[C:47]([CH3:48])[C:38]([C:32](=[O:31])[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:39]2[C:9]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=2)=[CH:44][CH:43]=1

Participants

3

Reactant 2

HCID 86691567Ethyl 2-tert-butoxy-2-(7-chloro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetateHCID 866915692-(6-Chloro-7-fluoro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate

Product 1

HCID 67126202Ethyl 2-(7-chloro-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetate

Procedure

Ethyl 2-(7-chloro-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetate was prepared in a similar manner to 2-(6-chloro-7-fluoro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate of Example 99, except using ethyl 2-tert-butoxy-2-(7-chloro-3-methyl-1-(trifluoromethylsulfonyloxy) naphthalen-2-yl)acetate. 1H-NMR: (400 MHz, CDCl3): δ 8.05 (d, J=2.0 Hz, 1H), 7.79 (d, J=8.6 Hz, 1H), 7.74 (s, 1H), 7.58 (dd, J=8.6, 2.0 Hz, 1H), 4.41 (q, J=7.0 Hz, 2H), 2.48 (s, 3H), 1.40 (t, J=7.0 Hz, 3H). 19F-NMR: (377 MHz, CDCl3): δ−73.2 (s)

Sources & evidence

ORD record
ord-fa8a7f6695a14e1da1c45f0f8a85d2a8
Source dataset
uspto-grants-2015_08
Patent number
US09102614B2

Reaction notes

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