1,2-Dibromoethane → HCID 86717739, compound

HRID 1468656Notes

Reaction equation

HRID 1468656 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:12])[CH:5]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:7]=1.[Br:13][CH2:14][CH2:15]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:13][CH2:14][CH2:15][O:12][C:4]1[CH:5]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:7]=[C:2]([F:1])[CH:3]=1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 84662442HCID 84662442, compound

Product 1

HCID 86717739HCID 86717739, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-fluoro-5-methylsulfonyl-phenol (4.2 g, 22.08 mmol), 1,2-dibromoethane (24 ml, 27.7 mmol) and potassium carbonate (6.1 g, 44.2 mmol) in acetonitrile (36 ml) was divided into 6 aliquots which were each heated under microwave radiation at 120° C. for 30 min. The reaction mixtures were cooled to room temperature, filtrated and pooled. The volatiles were evaporated, aqueous sodium carbonate (100 ml, 10%) was added and the mixture was extracted with ethyl acetate (2×100 ml). The combined organic phase was washed with brine (75 ml), dried (Na2SO4) and evaporated. Purification by flash column chromatography (ethyl acetate/isooctane, 0:1 to 1:0) gave the title compound (4.77 g, 73%). MS m/z (relative intensity, 70 eV 298 (M+, 18), 296 (M+, 18), 109 (bp), 107 (99), 82 (15).

Workup

  1. customThe reaction mixtures
  2. temperaturewere cooled to room temperature
  3. filtrationfiltrated
  4. customThe volatiles were evaporated
  5. additionaqueous sodium carbonate (100 ml, 10%) was added
  6. extractionthe mixture was extracted with ethyl acetate (2×100 ml)
  7. washThe combined organic phase was washed with brine (75 ml)
  8. dry with materialdried (Na2SO4)
  9. customevaporated
  10. customPurification by flash column chromatography (ethyl acetate/isooctane, 0:1 to 1:0)

Sources & evidence

ORD record
ord-24eb90de28e44cb08788143caf681ffc
Source dataset
uspto-grants-2015_04
Patent number
US09006227B2

Reaction notes

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