Chlorosuccinimide → 2-Chloro-5-[2-(3-chloro-phenyl)-ethoxy]-4-methoxy-benzoic acid methyl ester

HRID 2405225Notes

Reaction equation

HRID 2405225 reaction equation
OC1C=C(C=CC=1OC)C(OC)=O.[Cl:14]C1C=C(CCO)C=CC=1.[CH3:24][O:25][C:26](=[O:45])[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=2)[CH:28]=1.ClN1C(=O)CCC1=O>C(Cl)Cl.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[CH3:24][O:25][C:26](=[O:45])[C:27]1[CH:28]=[C:29]([O:35][CH2:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=2)[C:30]([O:33][CH3:34])=[CH:31][C:32]=1[Cl:14]

Participants

7

Reactant 4

HCID 31398ChlorosuccinimideHCID 78856m-Chlorophenethylic alcoholHCID 4056967Methyl 3-hydroxy-4-methoxybenzoateHCID 670762963-[2-(3-Chloro-phenyl)-ethoxy]-4-methoxy-benzoic acid methyl ester

Product 1

HCID 670763362-Chloro-5-[2-(3-chloro-phenyl)-ethoxy]-4-methoxy-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl 3-hydroxy-4-methoxybenzoate and 2-(3-chlorophenyl)-ethanol were reacted in analogy to step 1 of example 1. The obtained 3-[2-(3-chloro-phenyl)-ethoxy]-4-methoxy-benzoic acid methyl ester (300 mg, 0.935 mmol), N-chloro-succinimide (381 mg, 2.81 mmol), and zirconium tetrachloride (129 mg, 0.57 mmol) were suspended in DCM (4 ml) and the mixture was stirred under reflux for 5 h until the starting material was used up. The mixture was partitioned between EA and a saturated aqueous sodium hydrogencarbonate solution, the aqueous phase extracted with EA, and the combined organic extracts were dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by silica chromatography (HEP/EA gradient) to give 118 mg of the title compound.

Workup

  1. temperatureunder reflux for 5 h until the starting material
  2. customThe mixture was partitioned between EA
  3. extractiona saturated aqueous sodium hydrogencarbonate solution, the aqueous phase extracted with EA
  4. dry with materialthe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe residue was purified by silica chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-dbcafa86ccd848248ca70bd1eb6433cb
Source dataset
uspto-grants-2014_08
Patent number
US08802720B2

Reaction notes

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