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

HRID 991116Notes

Reaction equation

HRID 991116 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 carefully quenched with ice cold water and acidified with concentrated HCl. The product was extracted with choroform, 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 carefully quenched with ice cold water
  2. extractionThe product was extracted with choroform
  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-8fd3dae1eaaf40fcb8e5777cfe42cc77
Source dataset
uspto-grants-2002_10
Patent number
US06462073B2

Reaction notes

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