Methanol → 3'-(Chloromethyl)-2,6-dimethyl-4-[3-(methylsulfonyl)propoxy]biphenyl

HRID 1848779Notes

Reaction equation

HRID 1848779 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:5]=[C:4]([CH3:16])[C:3]=1[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23]O)[CH:18]=1.P(Cl)(Cl)([Cl:27])=O.O.CO>CN(C)C=O>[Cl:27][CH2:23][C:19]1[CH:18]=[C:17]([C:3]2[C:2]([CH3:1])=[CH:7][C:6]([O:8][CH2:9][CH2:10][CH2:11][S:12]([CH3:15])(=[O:14])=[O:13])=[CH:5][C:4]=2[CH3:16])[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 962Water2×HCID 24813Phosphorus oxychlorideHCID 593425562',6'-Dimethyl-4'-(3-(methylsulfonyl)propoxy)(1,1'-biphenyl)-3-methanol

Product 1

HCID 862228633'-(Chloromethyl)-2,6-dimethyl-4-[3-(methylsulfonyl)propoxy]biphenylYield 91.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To {2′,6′-dimethyl-4′-[3-(methylsulfonyl)propoxy]biphenyl-3-yl}methanol (30.0 g) was added N,N-dimethylformamide (90 mL), and the mixture was stirred for 20 min. To the mixture was added dropwise at 25° C. a separately prepared solution of phosphorus oxychloride (17.2 g) in N,N-dimethylformamide (54.0 mL), and the mixture was stirred at 25° C. for 4 hr. Water (30 mL) and then methanol (30 mL) were added dropwise. Seed crystal was added, and the mixture was stirred for 1 hr. Methanol (120 mL) was added, and the mixture was stirred for 1 hr. Then, water (120 mL) was added dropwise, and the mixture was stirred for 1 hr. The precipitated crystals were collected by filtration, and washed with water (300 mL). The obtained crystals were suspended in water (300 mL), and the mixture was stirred. The crystals were collected by filtration, washed with water (300 mL), and dried at 60° C. to give 3′-chloromethyl-2,6-dimethyl-4-[3-(methylsulfonyl)propoxy]biphenyl (28.8 g).

Workup

  1. stirringthe mixture was stirred at 25° C. for 4 hr
  2. additionSeed crystal was added
  3. stirringthe mixture was stirred for 1 hr
  4. stirringthe mixture was stirred for 1 hr
  5. stirringthe mixture was stirred for 1 hr
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with water (300 mL)
  8. stirringthe mixture was stirred
  9. filtrationThe crystals were collected by filtration
  10. washwashed with water (300 mL)
  11. customdried at 60° C.

Sources & evidence

ORD record
ord-35e040e799b541edac5cdd8bbd4fed44
Source dataset
uspto-grants-2015_02
Patent number
US08952185B2

Reaction notes

Loading…