Carbon Dioxide → HCID 70650712, compound

HRID 1446712Notes

Reaction equation

HRID 1446712 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[C:4]([F:12])[CH:3]=1.S(=O)(=O)(O)O.[CH2:18]=[C:19]([CH3:21])[CH3:20].C(=O)=O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:19]([CH3:21])([CH3:20])[CH3:18])=[O:10])=[C:4]([F:12])[CH:3]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 1118Sulfuric AcidHCID 8255Isobutylene2×HCID 140537922-(4-Bromo-2-fluorophenyl)acetic acid

Product 1

HCID 70650712HCID 70650712, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Combine 4-bromo-2-fluoro-phenyl acetic acid (15 g, 0.064 mol), dichloromethane (30 mL) and concentrated sulfuric acid (1.1 mL) in a 2 L stainless steel Parr® vessel. Cool the vessel and contents in a dry ice-acetone bath. Freshly distill isobutene (60 mL) with dry ice-acetone condenser and add the isobutene to the cooled Parr® vessel. Seal and pressurize the vessel with nitrogen (20 psig), agitate while allowing the reaction to warm to room temperature and continue agitation at room temperature for 18 hours. Cool the vessel to 10-15° C. with dry ice, vent, and carefully add 150 mL of ice-cold saturated sodium carbonate solution and mix. Decant vessel contents, rinse vessel with dichloromethane (100 mL), agitate mixture and separate the phases. Extract aqueous phase twice with 100 mL portions of dichloromethane, combine organic layers and wash with aqueous saturated sodium chloride, dry over MgSO4 and concentrate to produce 18.61 g (90%) of the title compound as a light orange oil. MS (ES) m/z 288/290, (M+1).

Workup

  1. temperatureCool the vessel and contents in a dry ice-acetone bath
  2. customSeal
  3. customthe reaction
  4. customat room temperature
  5. customfor 18 hours
  6. additionmix
  7. customDecant vessel contents
  8. washrinse vessel with dichloromethane (100 mL)
  9. stirringagitate mixture
  10. customseparate the phases
  11. washwash with aqueous saturated sodium chloride
  12. dry with materialdry over MgSO4
  13. concentrationconcentrate

Sources & evidence

ORD record
ord-8afa119e1df547fcb6aa3c96c4d54480
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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