Dimethyl Sulfide → HCID 67244628, compound

HRID 2425585Notes

Reaction equation

HRID 2425585 reaction equation
CSC.[CH3:4][C:5]([CH3:21])([C:11]1[CH:16]=[CH:15][C:14]([I:17])=[C:13]([O:18][CH2:19][CH3:20])[CH:12]=1)[C:6](OCC)=[O:7].CC(O)C>C(OCC)C>[CH2:19]([O:18][C:13]1[CH:12]=[C:11]([C:5]([CH3:21])([CH3:4])[CH2:6][OH:7])[CH:16]=[CH:15][C:14]=1[I:17])[CH3:20]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 3776IsopropanolHCID 67245448HCID 67245448, compound

Product 1

HCID 67244628HCID 67244628, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Boran dimethylsulfide (33 mL, 66 mmol, 2M in tetrahydrofuran) was added to a solution of ethyl dimethyl-(3-ethoxy-4-iodophenyl)acetate (4.83 g, 13.3 mmol) in ethyl ether (40 mL). The reaction was stirred at room temperature for 3 d and stirred for an additional hour with 2-propanol (10 mL) to quench the excess borane. The solution was partitioned between aqueous sodium bicarbonate and methylene chloride. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated to give 2-ethoxy-4-(2-hydroxy-1,1-dimethylethyl)iodobenzene (4.23 g, 99%) as a yellow oil.

Workup

  1. customto quench the excess borane
  2. customThe solution was partitioned between aqueous sodium bicarbonate and methylene chloride
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-14d056dd266d4b00914b0a737eb5f709
Source dataset
uspto-grants-2011_06
Patent number
US07964724B2

Reaction notes

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