Sodium Iodide → Carbonic acid iodomethyl ester 2,6-dibromo-4-cyanophenyl ester

HRID 843097Notes

Reaction equation

HRID 843097 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([Br:10])[C:3]=1[O:11][C:12](=[O:16])[O:13][CH2:14]Cl.[I-:17].[Na+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([C:8]#[N:9])[CH:5]=[C:4]([Br:10])[C:3]=1[O:11][C:12](=[O:16])[O:13][CH2:14][I:17]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 70170999Carbonic acid chloromethyl ester 2,6-dibromo-4-cyanophenyl ester

Product 1

HCID 70170991Carbonic acid iodomethyl ester 2,6-dibromo-4-cyanophenyl esterYield 160.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
30 °C

Procedure

A solution of carbonic acid chloromethyl ester 2,6-dibromo-4-cyanophenyl ester (10.0 g, 27.1 mmol) in 30 mL of acetone was added sodium iodide (8.12 g, 54.1 mmol) and heated to 30° C. for 3 h. The acetone was removed, and the resulting slurry was treated with ether. The resulting white precipitated solids were filtered off, and the filtrate was then concentrated to afford tannish solids which was recrystallized from ether/hexanes to afford white solids (20 g, 96%). 1H-NMR (300 MHz, CDCl3) δ (ppm): 6.09 (s, 2H), 7.90 (s, 2H). Mp=103-105° C.

Workup

  1. customThe acetone was removed
  2. additionthe resulting slurry was treated with ether
  3. customThe resulting white precipitated solids
  4. filtrationwere filtered off
  5. concentrationthe filtrate was then concentrated
  6. customto afford tannish solids which
  7. customwas recrystallized from ether/hexanes

Sources & evidence

ORD record
ord-47b0eb92815d4a35bf5047eaa7e277b6
Source dataset
uspto-grants-2002_04
Patent number
US06376548B1

Reaction notes

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