Triethylamine → 1-(Chloromethyl)-2-iodobenzene

HRID 2078000Notes

Reaction equation

HRID 2078000 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-e151fdb4520640efb09ccbb6286947ee
Source dataset
uspto-grants-2011_04
Patent number
US07928209B2

Reaction notes

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