Sodium Carbonate → 4-Fluoro-2-(furan-2-yl)benzonitrile

HRID 82783

Reaction equation

HRID 82783 reaction equation
Br[C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].COCCOC>[F:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([C:12]2[O:11][CH:15]=[CH:14][CH:13]=2)[CH:9]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1189392-Bromo-4-fluorobenzonitrileHCID 2734357Furan-2-boronic acid

Product 1

HCID 670430044-Fluoro-2-(furan-2-yl)benzonitrileYield 35%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Following the same procedure used for AUP01158-1, AUP01160-1 was prepared from 2-bromo-4-fluorobenzonitrile (5.0 g, 25.0 mmol), furan-2-ylboronic acid (3.36 g, 30.0 mmol), Pd2(dba)3 (100 mg), 1,2-dimethoxyethane (25 mL) and 2M Na2CO3 (40 mL). The crude was purified by Combiflash chromatography (24 g column, 8 g silica., gradient of eluent from PE to PE/EtOac 9/1) to give the title compound as a light yellow solid. This solid had to be purified an ultimate time by drying under vacuum at 40° C. for 5 days. Finally, pure expected compound was obtained as a white off solid in 35% yield (1.65 g); mp 55-56° C.; 1H NMR (270 MHz, CDCl3) δ 6.58-6.59 (1H, m, ArH), 7.02 (1H, td, J=2.7 and 8.0 Hz, ArH), 7.40 (1H, d, J=3.6 Hz, ArH), 7.57 (1H, s, ArH), 7.62 (1H, d, J=2.7 Hz, ArH), 7.70 (1H, dd, J=5.5 and 7.7 Hz, ArH); HRMS (ESI) calcd. for C11H7FNO (M+H)+188.0506. found 188.0513.

Workup

  1. customThe crude was purified by Combiflash chromatography (24 g column, 8 g silica., gradient of eluent from PE to PE/EtOac 9/1)

Sources & evidence

ORD record
ord-4a59a6221b7449d091e65b8568a58f80
Source dataset
uspto-grants-2014_09
Patent number
US08846737B2

Linked notes

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