3-Bromo-4-fluorobenzonitrile → Tert-butyl{4-chloro-2-[(5-cyano-2-fluorophenyl)ethynyl]phenoxy}acetate

HRID 2390123

Reaction equation

HRID 2390123 reaction equation
[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[CH:17])([CH3:4])([CH3:3])[CH3:2].Br[C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[F:28])[C:23]#[N:24]>>[C:1]([O:5][C:6](=[O:18])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][C:20]1[CH:21]=[C:22]([C:23]#[N:24])[CH:25]=[CH:26][C:27]=1[F:28])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 1235793-Bromo-4-fluorobenzonitrileHCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×

Product 1

HCID 58521989Tert-butyl{4-chloro-2-[(5-cyano-2-fluorophenyl)ethynyl]phenoxy}acetate

Procedure

Following the general method as outlined in Intermediate 19, starting from tert-butyl(4-chloro-2-ethynylphenoxy)acetate (Intermediate 3) and 3-bromo-4-fluorobenzonitrile (ABCR), the title compound was obtained as a beige solid after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc

Sources & evidence

ORD record
ord-433e1ee34cc843729087b0b27f6e385e
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Linked notes

Loading…