Hydrochloric Acid → Methyl 5-(3-fluoro-4-vinylphenyl)nicotinate

HRID 661215Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH2:9])=[C:4]([F:10])[CH:3]=1.Cl.[CH3:12][O:13][C:14]([C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[N:20][CH:21]=1)=[O:15].Cl.C(=O)([O-])[O-].[K+].[K+]>>[F:10][C:4]1[CH:3]=[C:2]([C:18]2[CH:19]=[N:20][CH:21]=[C:16]([CH:17]=2)[C:14]([O:13][CH3:12])=[O:15])[CH:7]=[CH:6][C:5]=1[CH:8]=[CH2:9]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 11430Potassium Carbonate

HCID 166607744-Bromo-1-ethenyl-2-fluorobenzene

HCID 66890177[5-(Methoxycarbonyl)pyridin-3-yl]boronic acid hydrochloride

Product 1

HCID 58116499Methyl 5-(3-fluoro-4-vinylphenyl)nicotinate

Procedure

2.5 g (11.2 mmol) of 4-bromo-2-fluoro-1-vinylbenzene were reacted according to General Method 1A with 3.2 g (14.5 mmol) of [5-(methoxycarbonyl)pyridin-3-yl]boronic acid hydrochloride. The release of the hydrochloride was achieved by additional addition of 1.70 g (12.3 mmol) of potassium carbonate. Yield: 1.9 g (61% of theory)

Sources & evidence

ORD record: ord-05d80582f03b4f8facb1c032ebfd67a1
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084469B2

Reaction notes

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