4-Chlorophenol → 1-Chloro-4-{[(4-chlorophenoxy)methyl]sulfanyl}benzene

HRID 247052Notes

Reaction equation

HRID 247052 reaction equation
Br[CH2:2][S:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1.CC(C)([O-])C.[K+].[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1>CN(C=O)C>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([S:3][CH2:2][O:24][C:21]2[CH:22]=[CH:23][C:18]([Cl:17])=[CH:19][CH:20]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 135300861-Bromomethylthio-4-chlorobenzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 124395131-Chloro-4-{[(4-chlorophenoxy)methyl]sulfanyl}benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1-Bromomethylthio-4-chlorobenzene (20 mmol) in DMF (10 ml) was added with stirring at room temperature to a solution prepared from potassium tert-butoxide (20 mmol) and 4-chlorophenol (20 mmol) in DMF (50 ml). The resultant mixture was stirred at 80° C. for 1 h, the solvent was then distilled off, the residue triturated with water, the residual material extracted with chloroform, the dried (MgSO4) chloroform solution evaporated and the residue distilled; yield 3.65 g (64%), b.p. 135°-140° C./0.01 mmHg. 1H NMR (CDCl3): δ 5.29 (CH2), 6,6-7.4 (Ph's). MS [70 eV, m/Z (rel. int.)]; 2.84 (3,M), 159(36), 157 (100), 111 (15), 105 (13), 75 (21).

Workup

  1. distillationthe solvent was then distilled off
  2. customthe residue triturated with water
  3. extractionthe residual material extracted with chloroform
  4. dry with materialthe dried (MgSO4) chloroform solution
  5. customevaporated
  6. distillationthe residue distilled

Sources & evidence

ORD record
ord-0d6c6b6774b24da1947e1e8a18caa156
Source dataset
uspto-grants-1987_11
Patent number
US04705791

Reaction notes

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