2,4-Difluorophenylacetone → (S)-ethyl 2-tert-butoxy-2-(5,7-difluoro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate

HRID 926190Notes

Reaction equation

HRID 926190 reaction equation
BrC1C=C2C(=CC=1)[C:8]([O:12][S:13]([C:16]([F:19])([F:18])[F:17])(=[O:15])=[O:14])=[C:7]([C@H:20]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:21]([O:23][CH2:24][CH3:25])=[O:22])C(C)=C2.[F:32][C:33]1[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=1[CH2:40][C:41](=O)[CH3:42]>>[C:27]([O:26][C@@H:20]([C:7]1[C:41]([CH3:42])=[CH:40][C:34]2[C:35](=[CH:36][C:37]([F:39])=[CH:38][C:33]=2[F:32])[C:8]=1[O:12][S:13]([C:16]([F:19])([F:17])[F:18])(=[O:14])=[O:15])[C:21]([O:23][CH2:24][CH3:25])=[O:22])([CH3:28])([CH3:29])[CH3:30]

Participants

3

Reactant 2

HCID 27348812,4-DifluorophenylacetoneHCID 89681724(S)-ethyl 2-(6-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate

Product 1

HCID 89681775(S)-ethyl 2-tert-butoxy-2-(5,7-difluoro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate

Procedure

(S)-ethyl 2-tert-butoxy-2-(5,7-difluoro-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate was prepared in a similar was as (S)-ethyl 2-(6-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate in Example 20, except using 1-(2,4-difluorophenyl)propan-2-one instead of 1-(3-bromophenyl)propan-2-one. 1H-NMR: 400 MHz, (CDCl3) δ: 7.82 (s, 1H), 7.39 (d, J=5.47 Hz, 1H), 6.99 (m, 1H), 5.63 (s, 1H), 4.18 (m, 2H), 2.49 (s, 3H), 1.11 (s+t, 12H). 19F-NMR: 377 MHz, (CDCl3) δ: −73.27 (s, 3F), −109.1 (m, 1F), −117.5 (m, 1F).

Sources & evidence

ORD record
ord-fdb87dd86e2645e183732834619e78c5
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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