Pyridine → Carbonic acid chloromethyl ester 2,6-dibromo-4-cyanophenyl ester

HRID 843096

Reaction equation

HRID 843096 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Br:11])[C:9]=1[OH:10])[C:5]#[N:6].N1C=CC=CC=1.[Cl:18][CH2:19][O:20][C:21](Cl)=[O:22]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[C:8]([Br:11])[C:9]=1[O:10][C:21](=[O:22])[O:20][CH2:19][Cl:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15531BromoxynilHCID 62754Chloromethyl chloroformate

Product 1

HCID 70170999Carbonic acid chloromethyl ester 2,6-dibromo-4-cyanophenyl esterYield 94%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 3,5-dibromo-4-hydroxybenzonitrile (10.0 g, 36.1 mmol) in 180 mL of chloroform was added pyridine (2.92 ml, 36.1 mmol). Chloromethylchloroformate (5.2 mL 60 mmol) was then added over 5 min. The mixture was allowed to stir at room temperature for 12 h. The reaction was then washed with 1% HCl aq, water, and brine. The organic layer was then dried over sodium sulfate, filtered, and evaporated to afford a white solid (12.5 g) in 94% yield. 1H-NMR (300 MHz, CDCl3) δ (ppm): 5.87 (d, 2H), 7.90 (s, 2H). 13C-NMR (300 MHz, CDCl3) δ (ppm): 73.58, 113.87, 115.68, 119.01, 136.40, 149.53, 149.71. Mp=83-85° C.

Workup

  1. washThe reaction was then washed with 1% HCl aq, water, and brine
  2. dry with materialThe organic layer was then dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-cbf866c32fc24cc9a737db02655fd5d0
Source dataset
uspto-grants-2002_04
Patent number
US06376548B1

Linked notes

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