4-Bromoanisole → HCID 60209035, compound

HRID 1484292Notes

Reaction equation

HRID 1484292 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[CH:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.[Br:18][C:19]1[CH:24]=[CH:23][C:22]([O:25]C)=[CH:21][CH:20]=1.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl.CN(C=O)C>[Br:18][C:19]1[CH:20]=[CH:21][C:22]([OH:25])=[C:23]([C:9](=[O:11])[CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[CH:24]=1

Participants

7

Reactant 4

HCID 77304-BromoanisoleHCID 65578Oxalyl chlorideHCID 676173-Fluorophenylacetic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 60209035HCID 60209035, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Fluorophenylacetic acid (4.90 g, 32.07 mmoles) was dissolved in 50 ml dichloromethane. To this mixture, oxalylchloride (3.5 ml, 40.08 mmoles) and DMF (3 drops) were added at 0° C. and stirred for 30 min. The solvent was evaporated and dissolved in 50 ml dichloromethane. To this mixture, 4-bromoanisole (5.0 g, 26.72 mmoles) was added and cooled to 0° C. At 0° C. AlCl3 (5.3 g, 40.08 mmoles) was added and the reaction mixture was warmed to RT and stirred for 12 h. The reaction mixture was quenched by the addition of 2N HCl, extracted with ethyl acetate, dried over sodium sulphate and concentrated. The crude product was purified by column chromatography with ethyl acetate:petroleum ether to afford the title compound as off-white solid (6.6 g, 80% yield. 1H-NMR (δ ppm, CDCl3, 400 MHz): δ 12.02 (s, 1H), 7.94 (d, J=2.4 Hz, 1H), 7.57 (dd, J=8.9, 2.4.1 Hz, 1H), 7.36 (m, 1H), 7.04 (m, 3H), 6.90 (d, J=8.9 Hz, 1H), 4.28 (s, 2H).

Workup

  1. customThe solvent was evaporated
  2. dissolutiondissolved in 50 ml dichloromethane
  3. customAt 0° C
  4. temperaturethe reaction mixture was warmed to RT
  5. stirringstirred for 12 h
  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 with ethyl acetate

Sources & evidence

ORD record
ord-ea62ecab6f42403c96a513280aed6020
Source dataset
uspto-grants-2016_08
Patent number
US09421209B2

Reaction notes

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