Chloroacetyl chloride → HCID 13259766, compound

HRID 2291728Notes

Reaction equation

HRID 2291728 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[OH:6][CH2:7][CH2:8][O:9][C:10](=[O:32])[C:11]1[CH:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][C:19]=2[Cl:28])[CH:14]=[CH:13][C:12]=1[N+:29]([O-:31])=[O:30].C(N(CC)CC)C>CCOCC.O>[Cl:1][CH2:2][C:3]([O:6][CH2:7][CH2:8][O:9][C:10](=[O:32])[C:11]1[CH:16]=[C:15]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:26])([F:25])[F:27])=[CH:20][C:19]=2[Cl:28])[CH:14]=[CH:13][C:12]=1[N+:29]([O-:31])=[O:30])=[O:4]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 13259764HCID 13259764, compound

Product 1

HCID 13259766HCID 13259766, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent3×

Procedure

Chloroacetyl chloride (3 g, 0.027 mole) was added dropwise to a stirred solution of [2-hydroxyethyl]5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate (8.1 g, 0.02 mole), triethylamine (2.5 g), and ether (150 ml). The heat given off during the reaction raised the temperature of the ether solution to reflux. After completion of addition, the mixture was kept at reflux for 10 min. The mixture then was allowed to cool to room temperature, poured into 200 ml of water, and 400 ml of ether was added. The ether extract was washed three times with water, dried CaSO4 and condentrated to 8.6 g of yellowish oil. The oil was column chromatographed through silica gel with 20% ethyl acetate-80% hexane as eluent to afford 3.2 g of pure [2-chloroacetoxyethyl]5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate, as a pale yellow gummy material; nmr (CDCl3) δ 4.16 (S, 2H), 4.50 (S, 4H), 6.98-8.18 (m, 6H); ir (CHCl3) 1752, 1765.

Workup

  1. temperatureto reflux
  2. additionAfter completion of addition
  3. temperatureat reflux for 10 min
  4. additionwas added
  5. extractionThe ether extract
  6. washwas washed three times with water, dried CaSO4
  7. customchromatographed through silica gel with 20% ethyl acetate-80% hexane as eluent

Sources & evidence

ORD record
ord-a07fc654523f44d1b18a7b006945e97b
Source dataset
uspto-grants-1989_01
Patent number
US04797505

Reaction notes

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