Potassium vinyltrifluoroborate → 2-Tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-4-vinylnaphthalen-2-yl)acetic acid

HRID 514125Notes

Reaction equation

Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:4]([CH:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C:20]([OH:22])=[O:21])[C:3]=1[CH3:28].[CH:29]([B-](F)(F)F)=[CH2:30].[K+]>>[C:24]([O:23][CH:19]([C:4]1[C:3]([CH3:28])=[C:2]([CH:29]=[CH2:30])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[C:20]([OH:22])=[O:21])([CH3:26])([CH3:27])[CH3:25]

Participants

Reactant 2

HCID 23679353Potassium vinyltrifluoroborate

HCID 671262332-(4-Bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid

Product 1

HCID 671263352-Tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-4-vinylnaphthalen-2-yl)acetic acid

Procedure

2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-4-vinylnaphthalen-2-yl)acetic acid (128) was prepared in a similar manner as 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetic acid of Example 125, except using potassium vinyltrifluoroborate in the Suzuki coupling reaction, giving the title compound (parent form). 1H NMR (400 MHz, DMSO-d6) δ 12.78 (s, broad, 1H), 8.13 (d, J=8.2 Hz, 1H), 7.73-7.65 (m, 2H), 7.54-7.48 (m, 2H), 7.41-7.36 (m, 2H), 7.20 (d, J=8.2 Hz, 1H), 7.11 (dd, J=18.0, 11.7 Hz, 1H), 5.87 (d, J=11.4 Hz, 1H), 5.41 (d, J=18.0 Hz, 1H), 5.09 (s, 1H), 2.50 (s, 3H), 0.94 (s, 9H). LCMS-ESI− (m/z): [2M-2H+Na]− calcd for C50H48Cl2NaO6: 839.3; Found: 839.2.

Workup

customin the Suzuki coupling reaction

Sources & evidence

ORD record: ord-4fd66ff865544ed3a08f4731b98f9cbe
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102614B2

Reaction notes

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