Tributylstannane → 4-(3,3,4,4,4-Pentafluorobutyl)benzenemethanol acetate

HRID 16479

Reaction equation

HRID 16479 reaction equation
[F:1][C:2]([F:8])([F:7])[C:3]([F:6])([F:5])I.[C:9]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]=[CH2:21])=[CH:16][CH:15]=1)(=[O:11])[CH3:10].C([SnH](CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[C:9]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][C:3]([F:6])([F:5])[C:2]([F:8])([F:7])[F:1])=[CH:18][CH:19]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 5948TributylstannaneHCID 9636IodopentafluoroethaneHCID 27351614-Vinylbenzyl acetate

Product 1

HCID 874686924-(3,3,4,4,4-Pentafluorobutyl)benzenemethanol acetateYield 31.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

At −78° C., pentafluoroiodoethane (2.09 g, 8.51 mmol)) was condensed into a pressure bottle. Toluene (5 mL), 4-ethenylbenzenemethanol acetate (1 g, 5.67 mmol), and tributyltin hydride (1.53 mL, 5.67 mmol) were added. The pressure bottle was sealed and irradiated for 30 hours using a 75 W lamp. The solvent was removed in vacuo. Flash chromatography of the residue gave 525 mg of 4-(3,3,4,4,4-pentafluorobutyl)benzenemethanol acetate; 1H NMR (300 MHz, CDCl3) δ 7.32 (d, 2H), 7.21 (d, 2H), 5.09 (s, 2H), 2.91 (m, 2H), 2.32 (m, 2H), 2.10 (s, 3H) ppm.

Workup

  1. customAt −78° C.
  2. customcondensed into a pressure bottle
  3. customThe pressure bottle was sealed
  4. customirradiated for 30 hours
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-72789da0bacf460985824c4d250ad728
Source dataset
uspto-grants-2010_06
Patent number
US07737145B2

Linked notes

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