3-Bromo-2-fluorobenzyl Alcohol → Tert-butyl(4-chloro-2-{[2-fluoro-3-(hydroxymethyl)phenyl]ethynyl}phenoxy)acetate

HRID 2390127Notes

Reaction equation

HRID 2390127 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[C:21]([F:28])=[C:22]([CH2:26][OH:27])[CH:23]=[CH:24][CH:25]=1>>[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:25]=[CH:24][CH:23]=[C:22]([CH2:26][OH:27])[C:21]=1[F:28])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 269856463-Bromo-2-fluorobenzyl Alcohol2×HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate2×

Product 1

HCID 58521942Tert-butyl(4-chloro-2-{[2-fluoro-3-(hydroxymethyl)phenyl]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-2-fluorophenyl)methanol (Intermediate 11), the title compound was obtained as a dark brown sticky solid after purification by flash column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc.

Sources & evidence

ORD record
ord-34df86b5f5684d9aac60e86be550e07e
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Reaction notes

Loading…