Chlorosulfonic acid → HCID 89826088, compound

HRID 625698Notes

Reaction equation

HRID 625698 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[CH:4][C:3]=1[CH2:10][CH2:11][C:12]([OH:14])=O.ClS(O)(=O)=O>O>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([F:9])=[C:4]2[C:3]=1[CH2:10][CH2:11][C:12]2=[O:14]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 840459843-(2-Bromo-3,5-difluorophenyl)propanoic acid

Product 1

HCID 89826088HCID 89826088, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(2-Bromo-3,5-difluorophenyl)propanoic acid (from Step 2, 3.0 g) is stirred with chlorosulfonic acid (10 mL) for 2 hours at ambient temperature. The mixture is then added dropwise to a vigorously stirred mixture of water and ice (200 mL) and further stirred for 15 minutes. Extraction with diethyl ether, subsequent washing of the organic layer with water, NaOH (0.2 M), and brine, drying (Na2SO4) and removal of the solvent under reduced pressure gives the crude product (Yield 2.7 g) that is used in the next step without further purification. LC (METHOD 7): tR=1.16 min.

Workup

  1. extractionExtraction with diethyl ether
  2. washsubsequent washing of the organic layer with water, NaOH (0.2 M), and brine
  3. customdrying
  4. custom(Na2SO4) and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-38fefd198f4e4375b47069535a6c9d60
Source dataset
uspto-grants-2016_04
Patent number
US09308194B2

Reaction notes

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