Dimethylformamide → 2-Bromo-1,3-dimethyl-5-[3-(methylsulfonyl)propoxy]benzene

HRID 1848773Notes

Reaction equation

HRID 1848773 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].CC1C=CC(S(O[CH2:22][CH2:23][CH2:24][S:25]([CH3:28])(=[O:27])=[O:26])(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:22][CH2:23][CH2:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 819704-Bromo-3,5-dimethylphenolHCID 22732325(3-(Methylsulfonyl)propyl 4-methylbenzenesulfonate

Product 1

HCID 709269352-Bromo-1,3-dimethyl-5-[3-(methylsulfonyl)propoxy]benzeneYield 98.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
70 °C

Procedure

4-Bromo-3,5-dimethylphenol (400.0 g), 3-(methylsulfonyl)propyl 4-methylbenzenesulfonate (727.3 g) and potassium carbonate (357.6 g) were added to N,N-dimethylformamide (4000 mL), and the mixture was stirred. The mixture was heated to 70° C., stirred for 20 hr and cooled to 5° C. Water (2000 mL) was added dropwise at 10° C. or below, seed crystal was added, and water (4000 mL) was further added. The mixture was stirred at room temperature overnight and at 10° C. or below for 2 hr. The precipitated crystals were collected by filtration, washed with water (4000 mL) and dried to give the title compound (631.0 g).

Workup

  1. stirringstirred for 20 hr
  2. temperaturecooled to 5° C
  3. additionseed crystal was added
  4. stirringThe mixture was stirred at room temperature overnight and at 10° C. or below for 2 hr
  5. filtrationThe precipitated crystals were collected by filtration
  6. washwashed with water (4000 mL)
  7. customdried

Sources & evidence

ORD record
ord-ed6d04a3cbe64c5c857f040a97160d51
Source dataset
uspto-grants-2015_02
Patent number
US08952185B2

Reaction notes

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