Cesium carbonate → tert-Butyl[3-chloro-5-(3-chloro-5-cyanophenoxy)phenoxy]acetate

HRID 1157393Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[CH:16]=[C:15]([OH:17])[CH:14]=[C:13]([Cl:18])[CH:12]=2)[CH:9]=1)[C:5]#[N:6].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]>O1CCOCC1>[Cl:18][C:13]1[CH:14]=[C:15]([CH:16]=[C:11]([O:10][C:8]2[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=[C:2]([Cl:1])[CH:9]=2)[CH:12]=1)[O:17][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28]

Participants

Conditions

Temperature: 25 °C

Procedure

To a dioxane solution (5 mL) of 240 mg (0.857 mmol) of 3-chloro-5-(3-chloro-5-hydroxyphenoxy)benzonitrile (B-4) was added 363 mg (1.12 mmol) of cesium carbonate. This was stirred for 30 minutes at 25° C. and then 217 mg (1.12 mmol) of t-butyl bromoacetate (5-1) was added and the reaction was stirred until the LC/MS analysis indicated that the reaction was complete. The solids were then removed by filtration and the filtrate was concentrated and purified on a CombiFlash silica column eluted with an ethyl acetate:hexanes gradient to recover desired product 5-2 as an oil. Rf=0.9 (EtOAc:hexanes 1:4). MS: M+1=395. 1H NMR(CDCl3): 1.49 (s, 9H), 4.49 (s, 2H), 6.48 (t, 1H), 6.66 (t, 1H), 6.74 (t, 1H), 7.14 (m, 1H), 7.21 (m, 1H), 7.38 (m, 1H).

Workup

stirringthe reaction was stirred until the LC/MS analysis
customThe solids were then removed by filtration
concentrationthe filtrate was concentrated
custompurified on a CombiFlash silica column
washeluted with an ethyl acetate
customto recover desired product 5-2 as an oil

Sources & evidence

ORD record: ord-98658c4c36604553a9904e017403aad0
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807684B2

Reaction notes

Loading…