Hydrochloric Acid → HCID 72212751, compound

HRID 2200191Notes

Reaction equation

HRID 2200191 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4](I)[CH:3]=1.C([Sn](CCCC)(CCCC)[C:17]([O:19]CC)=[CH2:18])CCC.Cl>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:1][C:2]1[CH:3]=[C:4]([C:17](=[O:19])[CH3:18])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2590861-Fluoro-3-iodo-5-nitrobenzeneHCID 619414Stannane, tributyl(1-ethoxyethenyl)-

Product 1

HCID 72212751HCID 72212751, compoundYield 96.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Mix 1-fluoro-3-iodo-5-nitro-benzene (1 g, 3.75 mmol), tributyl(1-ethoxyvinyl)stannane (1.5 g, 4.15 mmol) and Pd(dppf)Cl2 (78 mg, 0.1 mmol) in toluene (5 mL) under N2. Stir at 100° C. under N2 atmosphere for 3 hrs. Cool to room temperature, add 1N HCl solution (5 mL) and stir for 20 min. Load directly onto silica gel column and purify by chromatography (EtOAc:PE=3:7) to give the title compound (660 mg, 96%).

Workup

  1. temperatureCool to room temperature
  2. stirringstir for 20 min
  3. customLoad directly onto silica gel column and purify by chromatography (EtOAc:PE=3:7)

Sources & evidence

ORD record
ord-28b9b4a381fa4a8397773095db5cd6e0
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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