5-(3-bromophenyl)pentanoic Acid → 2-bromo-6,7,8,9-tetrahydro-5H-benzo(7)annulen-5-one

HRID 2402384

Reaction equation

HRID 2402384 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)[CH:5]=[CH:6][CH:7]=1>ClC1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[C:12](=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 116804435-(3-bromophenyl)pentanoic Acid

Product 1

HCID 102433122-bromo-6,7,8,9-tetrahydro-5H-benzo(7)annulen-5-oneYield 43.6%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

To a solution of 5-(3-Bromo-phenyl)-pentanoic acid (6 g, 23 mmol) in chlorobenzene (300 mL) was added PPA (18 g) and the mixture was heated to reflux for 8 h. The mixture was cooled to rt and filtered. The filtrate was concentrated under reduced pressure then purified by silica gel chromatography using a solvent system of 10:1 petroleum ether/EtOAc to give 2-bromo-6,7,8,9-tetrahydro-benzocyclohepten-5-one (2.4 g, 42.9%). MS ESI calcd for C11H11BrO [M+H]+ 239, found 239.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 8 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthen purified by silica gel chromatography

Sources & evidence

ORD record
ord-371099ec59b34050b371a4b188286f0a
Source dataset
uspto-grants-2014_08
Patent number
US08796310B2

Linked notes

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