p-Bromochlorobenzene → [4-(4-Chloro-phenoxy)-phenylsulfanyl]-acetic acid ethyl ester

HRID 1595654Notes

Reaction equation

HRID 1595654 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12](=[O:22])[CH2:13][S:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[CH3:10].[H-].[Na+]>N1C=CC=CC=1.[Cu](Cl)Cl>[CH2:9]([O:11][C:12](=[O:22])[CH2:13][S:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:2]2[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=2)=[CH:17][CH:16]=1)[CH3:10]

Participants

6

Reactant 3

HCID 7806p-BromochlorobenzeneHCID 24758Sodium hydrideHCID 3742252Ethyl 2-[(4-hydroxyphenyl)sulfanyl]acetate

Product 1

HCID 11759095[4-(4-Chloro-phenoxy)-phenylsulfanyl]-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 1049PyridineSolvent

Procedure

A mixture of 4-bromo chlorobenzene (1.92 g, 10 mmol), (4-Hydroxy-phenylsulfanyl)-acetic acid ethyl ester (2.12 g, 10 mmol), sodium hydride (460 mg, 10 mmol) and copper(II) chloride (500 mg) was refluxed in anhydrous pyridine (50 ml) for 12 hrs. The reaction mixture was carefullly quenched with ice cold water and acidified with concentrated HCl. The product was extracted with chloroform, washed well with water; dried and concentrated. The product was purified by silica gel column chromatography by eluting with 30% ethyl acetate:hexane. Yield 2.5 g (77%); Colorless low melting solid; MS: 323 (M+H)+. Alternatively the title compound may be prepared from 4-(4-chloro-phenoxy)-benzenethiol and bromo ethyl acetate as described in example 83.

Workup

  1. customThe reaction mixture was carefullly quenched with ice cold water
  2. extractionThe product was extracted with chloroform
  3. washwashed well with water
  4. customdried
  5. concentrationconcentrated
  6. customThe product was purified by silica gel column chromatography
  7. washby eluting with 30% ethyl acetate
  8. customAlternatively the title compound may be prepared from 4-(4-chloro-phenoxy)-benzenethiol and bromo ethyl acetate

Sources & evidence

ORD record
ord-3c5b5ed53ae5418c887e42083b4617e9
Source dataset
uspto-grants-2001_09
Patent number
US06288086B1

Reaction notes

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