HCID 58887630, compound → HCID 21112938, compound

HRID 1767192Notes

Reaction equation

HRID 1767192 reaction equation
C([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH2:15][CH2:14][CH2:13][C:12]=2[C:16]2[CH:21]=[C:20]([Br:22])[CH:19]=[CH:18][C:17]=2[O:23]C)[CH:6]=1)C>ClCCl>[Br:22][C:20]1[CH:19]=[CH:18][C:17]([OH:23])=[C:16]([C:12]2[CH2:13][CH2:14][CH2:15][C:11]=2[C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[C:4]([OH:25])=[O:3])[CH:21]=1

Participants

3

Reactant 1

HCID 58887630HCID 58887630, compound

Product 1

HCID 21112938HCID 21112938, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-{2-[5-Bromo-2-(methoxy)-phenyl]-cyclopent-1-enyl}-benzoic acid ethyl ester (416 mg, 10.0 mmol) in dichloromethane (5 mL) was cooled under nitrogen to ˜40° C. and was treated with a molar solution of borontribromide in dichloromethane (20 mL, 20.0 mmol). The reaction mixture was then allowed to reach room temperature and kept stirring over night. The reaction mixture was then quenched with ice/water (50/50 mL) and more dichloromethane (30 mL) was added. After stirring vigorously for 1.5 hr. the organic layer was separated, dried (magnesium sulphate), evaporated down and chromatographed with 1% methanol in dichloromethane to give (300 mg, 80%).

Workup

  1. customto reach room temperature
  2. customThe reaction mixture was then quenched with ice/water (50/50 mL) and more dichloromethane (30 mL)
  3. additionwas added
  4. stirringAfter stirring vigorously for 1.5 hr
  5. customthe organic layer was separated
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated down
  8. customchromatographed with 1% methanol in dichloromethane
  9. customto give (300 mg, 80%)

Sources & evidence

ORD record
ord-d158a02cdf7640318e200340311277ce
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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