Dichloromethane → 7-Bromo-2,3-dihydro-1H-inden-1-one

HRID 928630Notes

Reaction equation

HRID 928630 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[CH:9]([OH:11])[CH2:8][CH2:7]2.ClCCl.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[CH2:8][CH2:7]2

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 583066807-Bromo-2,3-dihydro-1H-inden-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 145152987-Bromo-2,3-dihydro-1H-inden-1-one

Procedure

To a solution of 37.9 g (177 mmol) of 7-bromoindan-1-ol in 3500 ml of dichloromethane 194 g (900 mmol) of pyridinium chlorochromate was added. The resulting mixture was stirred at room temperature for 5 h, then passed through a silica gel pad (500 ml), and the elute was evaporated to dryness. Yield 27.6 g (74%) of a white crystalline solid. Anal. Calc for C9H7BrO: C, 51.22; H, 3.34. Found: C, 51.35; H, 3.41. 1H NMR (CDCl3): δ 7.51 (m, 1H, 6-H); 7.36-7.42 (m, 2H, 4,5-H); 3.09 (m, 2H, 3,3′-H); 2.73 (m, 2H, 2,2′-H).

Workup

  1. customthe elute was evaporated to dryness

Sources & evidence

ORD record
ord-4a1b083414234747852186a71c73ca06
Source dataset
uspto-grants-2016_03
Patent number
US09290519B2

Reaction notes

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