Dichloromethane → HCID 21112933, compound

HRID 1767204Notes

Reaction equation

HRID 1767204 reaction equation
C([O:3][C:4](=[O:24])[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]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22]C)[CH:6]=1)C.ClCCl>B(Br)(Br)Br>[OH:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:12]1[CH2:13][CH2:14][CH2:15][C:11]=1[C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[C:4]([OH:24])=[O:3]

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 695079153-[2-(2-Methoxy-phenyl)-cyclopent-1-enyl]-benzoic Acid Ethyl Ester

Product 1

HCID 21112933HCID 21112933, compound

Reagents, catalysts & solvents 1

HCID 25134Boron tribromideSolvent

Procedure

3-[2-(2-Methoxy-phenyl)-cyclopent-1-enyl]-benzoic acid ethyl ester (610 mg, 1.89 mmol) was dissolved in 1M boron tribromide in dichloromethane solution (18.9 ml, 18.9 mmol) and left at room temperature for 18 hours. The resulting solution was poured onto ice and extracted with dichloromethane. The organic extract was dried (MgSO4), evaporated to dryness and purified by chromatography using biotage with iso-hexane containing a gradient of ethyl acetate (20–40%) to yield the title compound as a light brown solid. (186 mg, 35%).

Workup

  1. additionThe resulting solution was poured onto ice
  2. extractionextracted with dichloromethane
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. customevaporated to dryness
  6. custompurified by chromatography

Sources & evidence

ORD record
ord-072be2acd1d542d4a01122db1c92107b
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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