4-Amino-3-fluorophenol → Tert-butyl 4-(4-amino-3-fluorophenoxy)picolinate

HRID 2042058Notes

Reaction equation

HRID 2042058 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].CC(C)([O-])C.[K+].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:18]=1>>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:18]=2)=[CH:4][C:3]=1[F:9]

Participants

4

Reactant 3

HCID 27359194-Amino-3-fluorophenolHCID 11806045tert-Butyl 4-chloropicolinateHCID 23665647Potassium tert-butoxide

Product 1

HCID 67253219Tert-butyl 4-(4-amino-3-fluorophenoxy)picolinateYield 93.6%

Procedure

By analogy to Example A2, 4-amino-3-fluorophenol (0.12 g, 0.53 mmol), potassium tert-butoxide (0.080 g, 0.71 mmol) and tert-butyl 4-chloropicolinate (159 mg, 0.53 mmol) were combined to provide tert-butyl 4-(4-amino-3-fluorophenoxy)picolinate (151 mg, 67% yield). MS (ESI) m/z: 305.0 (M+H+).

Sources & evidence

ORD record
ord-5e953c7bf5a64b86a24b1dd6744bf6ef
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

Loading…