Potassium Carbonate → HCID 70980333, compound

HRID 2271346Notes

Reaction equation

HRID 2271346 reaction equation
BrCC(O)C.Br[CH:7]([CH3:10])[CH2:8][OH:9].[F:11][C:12]1[CH:13]=[C:14]([OH:22])[CH:15]=[C:16]([S:18]([CH3:21])(=[O:20])=[O:19])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[F:11][C:12]1[CH:13]=[C:14]([CH:15]=[C:16]([S:18]([CH3:21])(=[O:19])=[O:20])[CH:17]=1)[O:22][CH:7]([CH3:10])[CH2:8][OH:9]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 117132-Bromopropan-1-olHCID 297401-Bromo-2-propanolHCID 84662442HCID 84662442, compound

Product 1

HCID 70980333HCID 70980333, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 1-bromo-2-propanol (70%) and 2-bromo-1-propanol (30%) (5.81 g, 41.8 mmol) was added to a solution of 3-fluoro-5-methylsulfonyl-phenol (1.59 g, 8.36 mmol) and potassium carbonate (2.37 g, 16.71 mmol) in dry dimethyl formamide (10 ml), the mixture was heated to 120° C. for 20 hours, the mixture was allowed to cool to ambient temperature and water (100 ml) was added. The aqueous phase was extracted with ethyl acetate (3×100 ml), the combined organic phase was washed with LiCl (5% aqueous solution, 4×50 ml), brine (50 ml) and dried with Na2SO4 and evaporated. Purification flash chromatography (isooctane:ethyl acetate 1:0 to 3:2). 0.65 g (mixture of 1-(3-fluoro-5-methylsulfonyl-phenoxy)propan-2-ol and 2-(3-fluoro-5-methylsulfonyl-phenoxy)propan-1-ol), 31%. MS m/z (relative intensity, 70 eV) 248 (M+, 14), 204 (54), 203 (bp), 191 (37), 190 (44).

Workup

  1. temperatureto cool to ambient temperature
  2. extractionThe aqueous phase was extracted with ethyl acetate (3×100 ml)
  3. washthe combined organic phase was washed with LiCl (5% aqueous solution, 4×50 ml), brine (50 ml)
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customPurification flash chromatography (isooctane:ethyl acetate 1:0 to 3:2)
  7. addition0.65 g (mixture of 1-(3-fluoro-5-methylsulfonyl-phenoxy)propan-2-ol and 2-(3-fluoro-5-methylsulfonyl-phenoxy)propan-1-ol), 31%

Sources & evidence

ORD record
ord-5dbee0aeb3484b6ea5412454603b2ebb
Source dataset
uspto-grants-2015_09
Patent number
US09120728B2

Reaction notes

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