Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → 4-(2-Chloroethoxy)-2',4'-difluoro-1,1'-biphenyl

HRID 1074214Notes

Reaction equation

HRID 1074214 reaction equation
[OH-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1.[Cl:18][CH2:19][CH2:20]OS(C1C=CC(C)=CC=1)(=O)=O>O.ClCCl>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:20][CH2:19][Cl:18])=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 14798Sodium HydroxideHCID 1009552',4'-Difluoro(1,1'-biphenyl)-4-ol

Product 1

HCID 45187454-(2-Chloroethoxy)-2',4'-difluoro-1,1'-biphenyl

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

The compound 2',4'-difluoro-4(2-chloroethoxy)biphenyl is prepared by a process wherein to a solution of 15 g of sodium hydroxide in 30 ml of water there is added 68.2 g of 4-(2',4'-difluorophenyl)phenol and 106 g of 2-chloroethyl-p-toluene-sulfonate. The mixture is heated to about 95°-100° C. while stirring (at 96°-98° C. an exothermic reaction occurs) and maintained at this temperature for 5 hours. The resulting material is diluted with dichloromethane, washed with water, and evacuated until dry. The crude product is crystallized using isopropyl alcohol to yield 62 g (69% of theory) of the final product. If a further crop (9 g) of pure product can be obtained from the mother liquor, the total yield of the product is 80% of theory.

Workup

  1. temperatureThe mixture is heated to about 95°-100° C.
  2. customan exothermic reaction
  3. temperaturemaintained at this temperature for 5 hours
  4. washwashed with water
  5. customevacuated
  6. customuntil dry
  7. customThe crude product is crystallized

Sources & evidence

ORD record
ord-61e69904fde2485d86634dd03aad944b
Source dataset
uspto-grants-1990_11
Patent number
US04973691

Reaction notes

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