Triethylamine → 1-(Chloromethyl)-2-iodobenzene

HRID 1673079Notes

Reaction equation

HRID 1673079 reaction equation
CS([Cl:5])(=O)=O.C(N(CC)CC)C.[I:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:5][CH2:16][C:15]1[CH:18]=[CH:19][CH:20]=[CH:21][C:14]=1[I:13]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1076292-Iodobenzylic alcoholHCID 516892Sodium Bicarbonate

Product 1

HCID 1010641-(Chloromethyl)-2-iodobenzeneYield 100.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (2.0 ml, 29 mmol) and triethylamine (3.6 ml, 26 mmol) were added to a solution of o-iodobenzyl alcohol (5.0 g, 21 mmol) in methylene chloride (50 ml) cooled to 0° C., and the mixture was stirred at that temperature for 19 hours. A 5% aqueous sodium hydrogencarbonate solution was added, and the resulting mixture was extracted with methylene chloride. The methylene chloride layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title compound (5.34 g).

Workup

  1. extractionthe resulting mixture was extracted with methylene chloride
  2. dry with materialThe methylene chloride layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d0c8da37b3b47e08bc57f8072de4f35
Source dataset
uspto-grants-2011_08
Patent number
US07999090B2

Reaction notes

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