1-chloro-4-methylsulfonylbenzene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 600 ml of chlorobenzene were added 272 g of anhydrous aluminum chloride and 229 g of methanesulfonyl chloride and the mixture was heated on a steam bath for 6 hours with stirring. The solution thus formed was poured into ice-water, and then the produce was extracted with 400 ml of methylene chloride. Methylene chloride was distilled off from the extract under reduced pressure. To the residue thus formed was added 300 ml of methanol, the mixture was cooled to 15° C., and crystals thus deposited were collected by filtration to provide 212 g 1-chloro-4-methylsulfonyl benzene having a melting point of 92° to 94° C. the mixture was heated on a steam bath for 6 hours The solution thus formed the produce was extracted with 400 ml of methylene chloride Methylene chloride was distilled off from the extract under reduced pressure To the residue thus formed crystals thus deposited were collected by filtration

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 600 ml of chlorobenzene were added 272 g of anhydrous aluminum chloride and 229 g of methanesulfonyl chloride and the mixture was heated on a steam bath for 6 hours with stirring. The solution thus formed was poured into ice-water, and then the produce was extracted with 400 ml of methylene chloride. Methylene chloride was distilled off from the extract under reduced pressure. To the residue thus formed was added 300 ml of methanol, the mixture was cooled to 15° C., and crystals thus deposited were collected by filtration to provide 212 g 1-chloro-4-methylsulfonyl benzene having a melting point of 92° to 94° C. the mixture was heated on a steam bath for 6 hours The solution thus formed the produce was extracted with 400 ml of methylene chloride Methylene chloride was distilled off from the extract under reduced pressure To the residue thus formed crystals thus deposited were collected by filtration

Conditions: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 600 ml of chlorobenzene were added 272 g of anhydrous aluminum chloride and 229 g of methanesulfonyl chloride and the mixture was heated on a steam bath for 6 hours with stirring. The solution thus formed was poured into ice-water, and then the produce was extracted with 400 ml of methylene chloride. Methylene chloride was distilled off from the extract under reduced pressure. To the residue thus formed was added 300 ml of methanol, the mixture was cooled to 15° C., and crystals thus deposited were collected by filtration to provide 212 g 1-chloro-4-methylsulfonyl benzene having a melting point of 92° to 94° C. the mixture was heated on a steam bath for 6 hours The solution thus formed the produce was extracted with 400 ml of methylene chloride Methylene chloride was distilled off from the extract under reduced pressure To the residue thus formed crystals thus deposited were collected by filtration

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A slurry of 5.72 g of 4-chlorophenyl methyl sulfone, 6.08 g of 4-benzylphenol and 4.56 g of K2CO3 in 150 ml of DMSO was heated at 160° C. for 8.5 hrs. The product (9.55 g, 94.1% yield) was recovered from the reaction mixture essentially as described in Example 18. Recrystallization from 2-propanol and then from aqueous acetic acid afforded purified 1-(4-(methylsulfonyl)phenoxy)-4-(phenylmethyl)benzene, mp 109°-110° C.

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 38.1 g of 4-chlorophenyl methyl sulfone and 37.2 g of 4-methoxyphenol dissolved in 150 ml of sulfolane was added 41.5 g of K2CO3. The mixture was heated at 160° C. for 7 hrs and then at 170° C. for 14.5 hrs and cooled. The mixture was poured into aqueous NaOH and the crystalline product collected by filtration, washed well with water and dried, which gave 47.5 g (85.3% yield) of product. Recrystallization from ethanol gave purified 4-(4-(methylsulfonyl)phenoxy)-1-methoxybenzene, mp 151.5°-153° C. cooled the crystalline product collected by filtration washed well with water dried

Conditions: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 9.54 g (0.0500 mole) of 4-chlorophenyl methyl sulfone, 13.0 g (0.0750 mole) of 4-bromophenol, 10.37 g (0.0750 mole) of K2CO3 and 150 ml of sulfolane was heated at 150° C. for 5.5 hrs and at 160° C. for 3.5 hrs. The reaction mixture was cooled and poured into a solution of 200 ml of 20% aqueous NaOH and 400 ml of water. The crystalline product was collected by filtration, washed well with water and dried, which gave 8.27 g (50.6% yield) of product. Recrystallization from ethanol afforded purified 1-bromo-4-(4-(methylsulfonyl)phenoxy)benzene, mp 127.5°-129° C. The reaction mixture was cooled The crystalline product was collected by filtration washed well with water dried

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 7.41 g (0.0576 mole) of 4-chlorophenol dissolved in 150 ml of DMSO was added 2.30 g (0.0576 mole) of NaOH. The mixture was heated to 60° C. and 10.0 g (0.0524 mole) of 4-chlorophenyl methyl sulfone was added. The reaction mixture was heated at 160° C. for 3 hrs and cooled. The mixture was poured into a solution of 400 ml of 2 Normal (N) aqueous NaOH and 300 ml of water. The crystalline product was collected by filtration, washed well with water, and dried, which gave 13.8 g (93.2% yield) of product, mp 109°-111° C. Recrystallization from ethanol afforded purified 4-(4-(methylsulfonyl)phenoxy)-1-chlorobenzene, mp 111°-112° C. The reaction mixture was heated at 160° C. for 3 hrs cooled The crystalline product was collected by filtration washed well with water dried