3-(3-Bromo-4-fluorophenyl)-2-propenoic acid → 3-[4-Fluoro-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)phenyl]acrylic Acid

HRID 988048Notes

Reaction equation

HRID 988048 reaction equation
[CH3:1][C:2]1[C:3](B(O)O)=[CH:4][C:5]2[C:6]([CH3:15])([CH3:14])[CH2:7][CH2:8][C:9]([CH3:13])([CH3:12])[C:10]=2[CH:11]=1.Br[C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][C:29]([OH:31])=[O:30])[CH:23]=[CH:24][C:25]=1[F:26]>>[F:26][C:25]1[CH:24]=[CH:23][C:22]([CH:27]=[CH:28][C:29]([OH:31])=[O:30])=[CH:21][C:20]=1[C:3]1[C:2]([CH3:1])=[CH:11][C:10]2[C:9]([CH3:13])([CH3:12])[CH2:8][CH2:7][C:6]([CH3:15])([CH3:14])[C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 6883113-(3-Bromo-4-fluorophenyl)-2-propenoic acidHCID 10037535(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)boronic acid

Product 1

HCID 697923013-[4-Fluoro-3-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)phenyl]acrylic AcidYield 63.3%

Procedure

In a manner similar to that of Example 1(c), by reaction of 2.0 g (8.12 mmol) of 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthylboronic acid (prepared in Example 5(a) of the patent WO-97/33881) and 1.54 g (6.25 mmol) of 3-(3-bromo-4-fluorophenyl)acrylic acid, 1.45 g (63%) of the expected compound was obtained in the form of a beige powder having a melting point of 181°-183° C.

Sources & evidence

ORD record
ord-3d1c5c4b84864d21838c6e03639b9c29
Source dataset
uspto-grants-2003_10
Patent number
US06632963B1

Reaction notes

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