HCID 10826647, compound → HCID 15480019, compound

HRID 1870525Notes

Reaction equation

HRID 1870525 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][C:8]([C:12]([O:14]C)=[O:13])=[CH:7][C:6]=2[CH:16]=1>CO.C1COCC1.[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][C:8]([C:12]([OH:14])=[O:13])=[CH:7][C:6]=2[CH:16]=1

Participants

5

Reactant 1

HCID 10826647HCID 10826647, compound

Product 1

HCID 15480019HCID 15480019, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of methyl 2-bromo-6,7-dihydro-5H-benzocyclohepten-8-carboxylate (1.0 g) in methanol (25 ml), THF (25 ml) and 1N NaOH (18 ml) was refluxed for 1 hour. The solvent was concentrated, acidified using 1N HCl, and extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over MgSO4. The solvent was evaporated in vacuo to give 2-bromo-6,7-dihydro-5H-benzocyclohepten-8-carboxylic acid (0.95 g) as colorless prisms.

Workup

  1. temperaturewas refluxed for 1 hour
  2. concentrationThe solvent was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-43d63127e7234bb398ca4b2f41717154
Source dataset
uspto-grants-2000_08
Patent number
US06096780

Reaction notes

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