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

HRID 1848774Notes

Reaction equation

HRID 1848774 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 (40.00 g), 3-(methylsulfonyl)propyl 4-methylbenzenesulfonate (72.71 g) and potassium carbonate (35.75 g) were added to N,N-dimethylformamide (400 mL), and the mixture was stirred. The mixture was heated to 70° C., stirred for 46 hr, and cooled to 5° C. Water (200 mL) was added dropwise at 10° C. or below, seed crystal (60 mg) was added, and water (400 mL) was continuously added. After stirring for 2 hr, the precipitated crystals were collected by filtration, washed with water (400 mL) and dried to give the title compound (63.08 g).

Workup

  1. stirringstirred for 46 hr
  2. temperaturecooled to 5° C
  3. stirringAfter stirring for 2 hr
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with water (400 mL)
  6. customdried

Sources & evidence

ORD record
ord-412eaa1f85424d02b770aaf7406de3df
Source dataset
uspto-grants-2015_02
Patent number
US08952185B2

Reaction notes

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