Acetic Acid → HCID 58368440, compound

HRID 1192529Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:25]([O:27][CH3:28])=[O:26])[C:5]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[C:19]([F:24])[CH:18]=2)=[C:6]([N+:14]([O-])=O)[C:7]=1[C:8]#[C:9][Si:10]([CH3:13])([CH3:12])[CH3:11].C(O)(=O)C>CO.O.C(OCC)(=O)C.[Fe]>[NH2:14][C:6]1[C:7]([C:8]#[C:9][Si:10]([CH3:12])([CH3:11])[CH3:13])=[C:2]([Cl:1])[CH:3]=[C:4]([C:25]([O:27][CH3:28])=[O:26])[C:5]=1[C:17]1[CH:18]=[C:19]([F:24])[CH:20]=[C:21]([F:23])[CH:22]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of methyl 4-chloro-3′,5′-difluoro-6-nitro-5-[(trimethylsilyl)ethynyl]biphenyl-2-carboxylate (4.6 g, 11 mmol) in methanol (46 mL), water (13 mL), and acetic acid (31 mL) was treated with iron (<10 micron) (3.0 g, 54 mmol) and heated at 60° C. for 2 hours. The reaction mixture was treated with additional iron (1.0 g, 18 mmol) and heated at 60° C. for 1 hour to drive the reaction to completion. The reaction mixture was diluted with ethyl acetate (50 mL) and filtered over celite. The filtrate was concentrated to a crude residue. The crude residue was diluted with ethyl acetate and filtered through a short plug of silica gel. The filtrate was concentrated to give the desired product (4.28 g, quantitative). LCMS for C19H19ClF2NO2Si (M+H)+: m/z=394.1; Found: 393.9.

Workup

temperatureheated at 60° C. for 1 hour
customthe reaction to completion
filtrationfiltered over celite
concentrationThe filtrate was concentrated to a crude residue
additionThe crude residue was diluted with ethyl acetate
filtrationfiltered through a short plug of silica gel
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-c63174384bd8454f836d939195160a00
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680108B2

Reaction notes

Loading…