1-(Chloromethyl)-4-iodobenzene → HCID 57548711, compound

HRID 1367726Notes

Reaction equation

HRID 1367726 reaction equation
I[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].[I:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1>CC(N(C)C)=O.[Zn].C1CC=CCCC=C1.C1CC=CCCC=C1.[Ni].IC1C=CC(CCCCCCCCCCCCCCCCCCO)=CC=1>[I:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:26][CH:25]=1

Participants

7

Reactant 2

HCID 8172111-(Chloromethyl)-4-iodobenzeneHCID 86625642HCID 86625642, compound

Product 1

HCID 57548711HCID 57548711, compoundYield 76%

Reagents, catalysts & solvents 4

HCID 23994ZincCatalystHCID 6433264Bis(1,5-cyclooctadiene)nickelCatalystHCID 1165580418-(p-Iodophenyl)octadecanolCatalystHCID 31374DimethylacetamideSolvent3×

Procedure

Zinc powder (70 mg, 1.06 mmol) was dried at 70° C. for 30 min in a sealed tube, then DMA (0.4 ml) and solid 12 (9 mg, 0.04 mmol) were added. After stirring for 10 min, a solution of ethyl 17-iodo-heptadecanoate 80 (300 mg, 0.71 mmol) in DMA (1.5 ml) was added and the reaction mixture was stirred in the sealed tube for 11 h at 70° C. In a 10-ml flask, Ni(COD)2 (10 mg, 0.04 mmol), (R)-(s-Bu)-Pybox (or (S)-(s-Bu)-Pybox) (23 mg, 0.07 mmol) and p-iodobenzyl chloride 82 (252 mg, 1 mmol) were dissolved in DMA (1.5 ml), then organozinc solution 81 was added via cannula. The mixture was stirred at room temperature for 15 h, and the reaction was quenched by addition of aqueous NH4Cl, extracted with EtOAc, the extract was dried over Na2SO4 and evaporated. Chromatography of the crude product in hexane-ether (97:3) yielded the compound 37 (276 mg, 76%).

Workup

  1. stirringthe reaction mixture was stirred in the sealed tube for 11 h at 70° C
  2. stirringThe mixture was stirred at room temperature for 15 h
  3. customthe reaction was quenched by addition of aqueous NH4Cl
  4. extractionextracted with EtOAc
  5. dry with materialthe extract was dried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-c3c51c7e1e64448e9c1e26e6e91eb2b3
Source dataset
uspto-grants-2011_02
Patent number
US07893286B2

Reaction notes

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