Phenylacetic Acid → HCID 12209494, compound

HRID 1476146Notes

Reaction equation

HRID 1476146 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl.CN(C=O)C>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[C:22]([C:8](=[O:10])[CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:23]=1

Participants

7

Reactant 4

HCID 999Phenylacetic AcidHCID 77304-BromoanisoleHCID 65578Oxalyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 12209494HCID 12209494, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Phenylacetic acid (1.09 g, 8.0 mmoles) was dissolved in 5 ml dichloromethane. To this mixture, oxalylchloride (1.01 g, 8.0 mmoles) and DMF (3 drops) were added at 0° C. and stirred for 30 min. The solvent was evaporated and dissolved in 5 ml dichloromethane. To this mixture, 4-bromoanisole (1 g, 5.34 mmoles) was added and cooled to 0° C. At 0° C. AlCl3 (1.06 g, 8.0 mmoles) was added and the reaction mixture was warmed to RT and stirred overnight. The reaction mixture was quenched by the addition of 2N HCl and extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was purified by column chromatography to afford the title compound as white solid (1 g, 66% yield). MP: 83-86° C. 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 11.56 (s, 1H), 8.01 (d, J=2.2Hz, 1H), 7.64 (dd, J=8.8, 2.5Hz, 1H), 7.32 (t, 2H), 7.29 (m,3H), 6.96 (d, J=8.8Hz, 1H), 4.43(s, 2H).

Workup

  1. customThe solvent was evaporated
  2. dissolutiondissolved in 5 ml dichloromethane
  3. customAt 0° C
  4. temperaturethe reaction mixture was warmed to RT
  5. stirringstirred overnight
  6. customThe reaction mixture was quenched by the addition of 2N HCl
  7. extractionextracted with ethyl acetate
  8. dry with materialdried over sodium sulphate
  9. concentrationconcentrated
  10. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-4cbdf66c8ac049a792c8cc1b6118458c
Source dataset
uspto-grants-2015_04
Patent number
US09018375B2

Reaction notes

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