HCID 67126073, compound → HCID 56602524, compound

HRID 514049Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:30])[C:6]([CH:19]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22]CC)=[O:21])=[C:7]2[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1.[F:31]C1C=C2C(=CC=1)C(=O)CC(C)C2>>[C:26]([O:25][CH:19]([C:6]1[C:5]([CH3:30])=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[C:11]([F:31])[CH:2]=2)[C:7]=1[C:12]1[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=1)[C:20]([OH:22])=[O:21])([CH3:28])([CH3:29])[CH3:27]

Participants

Reactant 2

HCID 67126073HCID 67126073, compound

HCID 86691544HCID 86691544, compound

Product 1

HCID 56602524HCID 56602524, compound

Procedure

2-tert-Butoxy-2-(1-(4-chlorophenyl)-6-fluoro-3-methylnaphthalen-2-yl)acetic acid (42) was prepared similarly to 2-(5-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid of Example 35, using 6-fluoro-3-methyl-3,4-dihydronaphthalen-1(2H)-one instead of 5-bromo-3-methyl-3,4-dihydronaphthalen-1(2H)-one. 1H-NMR: 400 MHz, (CD3OD) δ: 7.67 (s, 1H), 7.57 (s, 2H), 7.55 (as, 1H), 7.45 (dd, J=9.8, 2.8 Hz, 1H), 7.32 (d, J=8.4 Hz, 1H), 7.27 (dd, J=9.4, 5.2 Hz, 1H), 7.11 (td, J=9.0, 2.4 Hz, 1H) 5.16 (s, 1H), 2.60 (s, 3H), 0.98 (s, 9H). 19F-NMR: 377 MHz, (CD3OD) δ: −118.01 (s). LCMS-ESI− (m/z): [M—H]− calcd for C23H21ClFO3: 399.12; found: 399.19.

Sources & evidence

ORD record: ord-d9a81e1aef434a7b90146821499bacd4
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102614B2

Reaction notes

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