2,4-Difluoro-1-iodobenzene → HCID 57949494, compound

HRID 2427530Notes

Reaction equation

HRID 2427530 reaction equation
[CH2:1]([N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:13])[C:2]#[CH:3].[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1I>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[C:3]#[C:2][CH2:1][N:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]1=[O:13]

Participants

6

Reactant 2

HCID 1375192,4-Difluoro-1-iodobenzeneHCID 11194588HCID 11194588, compound

Product 1

HCID 57949494HCID 57949494, compoundYield 24.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

2-Prop-2-ynyl-2,3-dihydro-isoindol-1-one (50.0 mg, 0.29 mmol) was dissolved in triethylamine (2 mL). To this was added Pd(PPh3)4 (13 mg, 0.012 mmol), CuI (6.7 mg, 0.035 mmol) and 2,4-difluoro-1-iodo-benzene (52.0 μL, 0.438 mmol) and the reaction was allowed to stir overnight. The solvent was evaporated and the residue was purified by prep. TLC (30% EtOAc/Hexanes) to afford the title compound (20.0 mg, 24%) as a brown oil. 1H NMR (300 MHz, CDCl3): δ 7.90 (d, 1H), 7.45 (m, 4H), 6.84 (t, 2H), 4.72 (s, 2H), 4.59 (s, 2H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by prep

Sources & evidence

ORD record
ord-c1e434126a47446ebb4c908582e53741
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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