Water → Acifluorfen-methyl

HRID 1075317

Reaction equation

HRID 1075317 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:22]=[CH:21][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]([N+:18]([O-:20])=[O:19])=[C:12]([CH:17]=2)[C:13]([O:15][CH3:16])=[O:14])=[CH:5][CH:4]=1.[Cl:25]Cl.O>CCOCC>[Cl:25][C:5]1[CH:4]=[C:3]([C:2]([F:23])([F:24])[F:1])[CH:22]=[CH:21][C:6]=1[O:7][C:8]1[CH:9]=[CH:10][C:11]([N+:18]([O-:20])=[O:19])=[C:12]([CH:17]=1)[C:13]([O:15][CH3:16])=[O:14]

Participants

5

Reactant 3

HCID 962WaterHCID 24526ChlorineHCID 13209694Methyl 2-nitro-5-[4-(trifluoromethyl)phenoxy]benzoate

Product 1

HCID 91642Acifluorfen-methyl

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Methyl 5-(4-trifluoromethylphenoxy)-2-nitrobenzoate is stirred with a catalytic amount of ferric chloride. The reaction mixture was heated to 70° C. under a continuous stream of chlorine gas. After 2.5 hours, the mixture was taken up in ether, shaken with water and the organic phase was dried over MgSO4. The ether was evaporated to afford methyl 5-(2-chloro-4-trifluoromethylphenoxy)-2-nitrobenzoate. NMR (CDCl3)δ8.2-7 (m,6) 4.0 (2,3). TLC (40% ether/hexane) Rf ≈.4.

Workup

  1. dry with materialthe organic phase was dried over MgSO4
  2. customThe ether was evaporated

Sources & evidence

ORD record
ord-c85e0659d8554c0b9334c310b60f0b5a
Source dataset
uspto-grants-1983_07
Patent number
US04395570

Linked notes

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