Hydrochloric Acid → HCID 20071127, compound

HRID 981826Notes

Reaction equation

HRID 981826 reaction equation
[CH2:1]1[C:10](=[O:11])[CH2:9][C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.[H-].[Na+].Br[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([O:22][CH3:23])[CH:16]=1.Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.CN(C)C=O>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH:9]2[C:8]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:2][CH2:1][C:10]2=[O:11])=[CH:16][C:17]=1[O:22][CH3:23]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 682662-TetraloneHCID 27695675-Bromo-2-chloroanisole

Product 1

HCID 20071127HCID 20071127, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Charge an oven dried, argon flushed 25-mL two-necked round bottomed flask equipped with a stirring bar with β-tetralone (1.3095 grams, 8.9575 mmoles) and 5 mL dry dimethylformamide. Cool to 0° C. with an ice bath, add sodium hydride (0.4299 grams, 8.9575 mmoles, 50% oil dispersion) and stir for 25 minutes. Filter the solution through a 5 mL syringe equipped with a bed of celite (dried in an oven) via a double-ended needle into an oven dried, argon flushed 25-mL round bottomed flask equipped with a stirring bar and reflux condenser which had been charged with 4-bromo-2-methoxy-1-chlorobenzene (1.5871 grams, 7.166 mmoles), palladium acetate (0.0079 grams 0.0350 mmoles) and tri(ο-tolyl)phosphine (0.0213 grams, 0.070 mmoles). Heat at about 125° C. (oil bath) for 21 hours, cool to RT and add ethyl acetate and 2N HCl. Separate the layers, extract the aqueous layers with two portions of ethyl acetate, wash the combined organic layers with saturated sodium bicarbonate solution followed by saturated salt solution, dry over magnesium sulfate and concentrate using a Buchi rotavapor to produce the named product.

Workup

  1. additionCharge an oven
  2. customdried
  3. customargon flushed 25-mL two-necked round bottomed flask
  4. filtrationFilter the solution through a 5 mL syringe
  5. customequipped with a bed of celite (dried in an oven) via a double-ended needle into an oven
  6. customdried
  7. customargon flushed 25-mL round bottomed flask
  8. customequipped with a stirring bar
  9. temperaturereflux condenser which
  10. temperatureHeat at about 125° C. (oil bath) for 21 hours
  11. temperaturecool to RT
  12. customSeparate the layers
  13. extractionextract the aqueous layers with two portions of ethyl acetate
  14. washwash the combined organic layers with saturated sodium bicarbonate solution
  15. dry with materialdry over magnesium sulfate
  16. concentrationconcentrate
  17. customto produce the named product

Sources & evidence

ORD record
ord-3343812ada1841d488afe1d8393f6a12
Source dataset
uspto-grants-1991_02
Patent number
US04992591

Reaction notes

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