Diethyl Ether → Methoxycarbonylaminooxyacetic acid 2,6-dibromo-4-cyano-phenoxycarbonyloxymethyl ester

HRID 843099Notes

Reaction equation

HRID 843099 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.[CH3:17][O:18][C:19]([NH:21][O:22][CH2:23][C:24]([O-:26])=[O:25])=[O:20].[Na+].CCOCC>CN(C=O)C>[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:26][C:24](=[O:25])[CH2:23][O:22][NH:21][C:19]([O:18][CH3:17])=[O:20])=[O:16]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 23677256Sodium methoxycarbonylaminooxyacetateHCID 70170991Carbonic acid iodomethyl ester 2,6-dibromo-4-cyanophenyl ester

Product 1

HCID 86757969Methoxycarbonylaminooxyacetic acid 2,6-dibromo-4-cyano-phenoxycarbonyloxymethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of carbonic acid iodomethyl ester 2,6-dibromo-4-cyanophenyl ester (0.20 g, 0.43 mmol) in DMF (2 mL) was added sodium methoxycarbonylaminooxyacetate (0.89 g, 0.52 mmol). The mixture was stirred for 16 h. Ether was added to the reaction and washed with water then brine then dried over sodium sulfate, filtered, and concentrated to an oil. Silica gel chromatography (2:1 EtOAc:hexanes) afforded the desired product as a clear oil. 1H-NMR (300 MHz, CDCl3) δ (ppm): 3.80 (s, 3H), 4.57 (s, 2H), 5.99 (s, 2H), 7.90 (s, 2H), 8.02 (bs, 1H). Mp=110-111° C.

Workup

  1. washwashed with water
  2. dry with materialbrine then dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to an oil

Sources & evidence

ORD record
ord-2b22ff78a94145128fccdca38492e89b
Source dataset
uspto-grants-2002_04
Patent number
US06376548B1

Reaction notes

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