Bis(trifluoroacetoxy)iodobenzene → HCID 68685702, compound

HRID 1157136Notes

Reaction equation

HRID 1157136 reaction equation
FC(F)(F)C(OI(C1C=CC=CC=1)OC(=O)C(F)(F)F)=[O:4].[OH:22][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]2[C:32]=1[N:31]=[C:30]([C:33]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[O:34])[CH:29]=[CH:28]2>CC#N.O.C(Cl)Cl>[O:4]=[C:26]1[CH:25]=[CH:24][C:23](=[O:22])[C:32]2[N:31]=[C:30]([C:33]([O:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[O:34])[CH:29]=[CH:28][C:27]1=2

Participants

5

Reactant 2

HCID 102317Bis(trifluoroacetoxy)iodobenzeneHCID 68687888HCID 68687888, compound

Product 1

HCID 68685702HCID 68685702, compoundYield 91.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a stirred solution of [bis(trifluoroacetoxy)iodo]benzene (PIFA) (258 mg, 0.6 mmol) in MeCN/water 2:1 (3 ml) at 0° C. was added octyl 8-hydroxyquinoline-2-carboxylate (71 mg, 0.24 mmol) in CH2Cl2 (1 ml). The solution was stirred for 20 min, poured into CH2Cl2 (20 mL), washed with water and dried in vacuo to give octyl 5,8-dioxo-5,8-dihydroquinoline-2-carboxylate (69 mg, 90%).

Workup

  1. washwashed with water
  2. customdried in vacuo

Sources & evidence

ORD record
ord-b73e25f45351482d8b239c5aa134faf5
Source dataset
uspto-grants-2010_10
Patent number
US07807668B2

Reaction notes

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