Reaction #1583833

Reaction equation

potassium carbonate

N,N-dimethylformamide

2-(bromomethyl)-1-chloro-4-iodobenzene

product

2-(bromomethyl)-1-chloro-4-iodobenzene

N,N-dimethylformamide

→

title compound

methyl[(2-chloro-5-iodo-phenyl)methyl]carbamate

Solvents

methanol

Conditions

Workup

1. 1
   Temperaturecooled to room temperature
2. 2
   OtherThe reaction mixture was partitioned between diethyl ether (200 mL) and water (200 mL)
3. 3
   Otherthe organic layer was separated
4. 4
   Washwashed with water (3×50 mL)
5. 5
   Dryingdried over magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated under reduced pressure

Procedure

To a mixture of potassium carbonate (4.30 g, 53.3 mmol) in N,N-dimethylformamide (47 mL) and methanol (5 mL) at 50° C. was added a solution of 2-(bromomethyl)-1-chloro-4-iodobenzene (i.e. the product of Step A) (5.20 g, 15.7 mmol) in N,N-dimethylformamide (10 mL). The reaction mixture was heated at 110° C. for 1 h and then cooled to room temperature. The reaction mixture was partitioned between diethyl ether (200 mL) and water (200 mL), the organic layer was separated, washed with water (3×50 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the title compound as a yellow oil (4.32 g).

Source