Hydrochloric Acid → Methyl 5-[4-(difluoromethoxy)phenyl]nicotinate

HRID 220031Notes

Reaction equation

HRID 220031 reaction equation
[F:1][CH:2]([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7](Br)=[CH:6][CH:5]=1.Cl.[CH3:13][O:14][C:15]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[N:21][CH:22]=1)=[O:16].Cl.C(=O)([O-])[O-].[K+].[K+]>>[F:1][CH:2]([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:19]2[CH:20]=[N:21][CH:22]=[C:17]([CH:18]=2)[C:15]([O:14][CH3:13])=[O:16])=[CH:6][CH:5]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27370071-Bromo-4-(difluoromethoxy)benzeneHCID 66890177[5-(Methoxycarbonyl)pyridin-3-yl]boronic acid hydrochloride

Product 1

HCID 58116524Methyl 5-[4-(difluoromethoxy)phenyl]nicotinate

Procedure

10.0 g (44.8 mmol) of 4-(difluoromethoxy)bromobenzene were reacted according to General Method 3A with 14.6 g (67.3 mmol) of [5-(methoxycarbonyl)pyridin-3-yl]boronic acid hydrochloride. The release of the hydrochloride was achieved by additional addition of 6.80 g (49.3 mmol) of potassium carbonate. Yield: 8.6 g (67% of theory)

Sources & evidence

ORD record
ord-56ea15a4ab8c48bdb14ea66e371a9823
Source dataset
uspto-grants-2012_06
Patent number
US08202862B2

Reaction notes

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