Tetrahydrofuran → HCID 13279412, compound

HRID 2296412Notes

Reaction equation

HRID 2296412 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10](Cl)=[O:11].[Cl:25][C:26]1[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:27]=1[O:28][CH2:29][C:30]([O:32][CH2:33][CH2:34][O:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][OH:41])=[O:31].C(N(CC)CC)C.C1COCC1>CCOCC>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]([F:23])([F:24])[F:22])[CH:18]=[CH:17][C:3]=1[O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:14]([O-:16])=[O:15])=[C:9]([CH:13]=1)[C:10]([O:41][CH2:40][CH2:39][O:38][CH2:37][CH2:36][O:35][CH2:34][CH2:33][O:32][C:30](=[O:31])[CH2:29][O:28][C:27]1[CH:42]=[CH:43][C:44]([Cl:46])=[CH:45][C:26]=1[Cl:25])=[O:11]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 30177655-(2-Chloro-4-(trifluoromethyl)phenoxy)-2-nitrobenzoyl chlorideHCID 13279417HCID 13279417, compound

Product 1

HCID 13279412HCID 13279412, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

5-(2-Chloro-4-trifluoromethylphenoxy)-2-nitrobenzoyl chloride (4.0 g, 0.0105 mole) was added portionwise to a solution of 8-hydroxy-3,6-dioxaoctyl 2,4-dichlorophenoxyacetate (3.5 g, 0.103 mole), triethylamine (1.2 g, 0.103 mole) and THF (40 ml) over 5 mins. The resulting solution was held at reflux for 3 hrs. After the solvent was stripped off, the residue was taken into 2600 ml of ether, washed two times with NaHCO3 solution and two times with water. The ether solution was then dried over MgSO4 and concentrated to 5.9 g of 8-(2,4-dichlorophenoxyacetoxy)-3,6-dioxaoctyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate, a brownish gum; nmr (CDCl3) δ3.30-4.02 (m, 8H), 4.25-4.62 (m, 4H), 4.70 (S, 2H), 6.65-8.24 (m, 9H); ir (CHCl3) 1750, 1770 Cm-1.

Workup

  1. temperatureat reflux for 3 hrs
  2. washwashed two times with NaHCO3 solution and two times with water
  3. dry with materialThe ether solution was then dried over MgSO4
  4. concentrationconcentrated to 5.9 g of 8-(2,4-dichlorophenoxyacetoxy)-3,6-dioxaoctyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate

Sources & evidence

ORD record
ord-7e7e4043b5cb4db48297d068f3ac0a68
Source dataset
uspto-grants-1984_01
Patent number
US04429146

Reaction notes

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