Sodium Iodide → HCID 57747241, compound

HRID 1163458Notes

Reaction equation

HRID 1163458 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1)=[O:4].[I-:20].[Na+].CCCCCC>COCCOC>[OH:15][C:8]1[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:5]([C:3](=[O:4])[CH2:2][I:20])=[CH:6][C:7]=1[C:16]([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 8058HexaneHCID 6161612-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-one

Product 1

HCID 57747241HCID 57747241, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of 6.54 g (20 mmol) of 2-bromo-1-(4-hydroxy-3,5-di-tert-butylphenyl)-ethanone in 25 ml of 1,2-dimethoxyethane, a solution of 3.14 g (21 mmol) of sodium iodide in 25 ml of 1,2-dimethoxyethane is added dropwise at room temperature. After the addition, stirring is continued for 16 hours at room temperature. Then 10 ml of hexane is added and, after stirring for additional 15 minutes, the precipitated salts are removed by filtration. The obtained solution is evaporated and the resulting residue is purified by recrystallization from hexane to give 5.21 g (70%) of compound 202, m.p. 88-89° C.

Workup

  1. additionAfter the addition
  2. stirringafter stirring for additional 15 minutes
  3. customthe precipitated salts are removed by filtration
  4. customThe obtained solution is evaporated
  5. customthe resulting residue is purified by recrystallization from hexane

Sources & evidence

ORD record
ord-02122310076245dbaabe818ee134b415
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Reaction notes

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