Acetic Acid → Acetic acid 2,6-dibromo-4-cyano-phenoxycarbonyloxymethyl ester

HRID 843098Notes

Reaction equation

HRID 843098 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]I.[C:17]([OH:20])(=[O:19])[CH3:18]>C([O-])(=O)C.[Ag+]>[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:13][CH2:14][O:20][C:17](=[O:19])[CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 70170991Carbonic acid iodomethyl ester 2,6-dibromo-4-cyanophenyl ester

Product 1

HCID 70171643Acetic acid 2,6-dibromo-4-cyano-phenoxycarbonyloxymethyl ester

Reagents, catalysts & solvents 1

HCID 11246Silver acetateCatalyst

Procedure

A solution of carbonic acid iodomethyl ester 2,6-dibromo-4-cyanophenyl ester (0.30 g, 0.65 mmol) in acetic acid (6.5 mL) was added silver acetate (0.33 g, 1.95 mmol). The mixture was stirred for 3 h. The slurry was concentrated to solids and washed with ether. The ether was concentrated to afford the desired product as white solids (240 mg). 1H-NMR (300 MHz, CDCl3) δ (ppm): 2.19 (s, 3H), 5.90 (s, 2H), 7.89 (s, 2H).). 13C-NMR (300 MHz, CDCl3) δ (ppm): 21.0, 83.3, 113.7, 115.7, 119.1, 136.4, 149.9, 169.4, 183.7. Mp=84-86° C.

Workup

  1. concentrationThe slurry was concentrated to solids
  2. washwashed with ether
  3. concentrationThe ether was concentrated

Sources & evidence

ORD record
ord-1ee0b9455efa4f89ad158d030da1aaed
Source dataset
uspto-grants-2002_04
Patent number
US06376548B1

Reaction notes

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