Sulfuric Acid → HCID 86724263, compound

HRID 594867Notes

Reaction equation

HRID 594867 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:21]=[CH:20][C:10]([O:11][CH2:12][C:13]2([C:17]([OH:19])=O)[CH2:16][CH2:15][CH2:14]2)=[CH:9][CH:8]=1>O>[Br:6][C:7]1[CH:8]=[C:9]2[C:10](=[CH:20][CH:21]=1)[O:11][CH2:12][C:13]1([CH2:14][CH2:15][CH2:16]1)[C:17]2=[O:19]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 84715327HCID 84715327, compound

Product 1

HCID 86724263HCID 86724263, compoundYield 36.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To sulfuric acid (5 mL) was added 1-[(4-bromophenoxy)methyl]cyclobutanecarboxylic acid (1.9 g, 6.6 mmol) at 0° C. in an ice bath. After stirring for 1 hour at room temperature, ice was added to the mixture portionwise. The mixture was diluted with water, and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (hexane:EtOAc=100:0-70:30) to give 6-bromo-4H-spiro[chromene-3,1′-cyclobutan]-4-one (649 mg).

Workup

  1. additionice was added to the mixture portionwise
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (hexane:EtOAc=100:0-70:30)

Sources & evidence

ORD record
ord-29da633089324ad0abf28baa2016947d
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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