Hydrochloric Acid → HCID 54498197, compound

HRID 1415890Notes

Reaction equation

HRID 1415890 reaction equation
B(Cl)(Cl)Cl.[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([OH:25])[CH:20]=[CH:21][C:22]=1[O:23][CH3:24].Cl>ClCCl.C1C=CC=CC=1>[OH:25][C:19]1[CH:18]=[C:17]([O:16][CH3:15])[C:22]([O:23][CH3:24])=[CH:21][C:20]=1[C:10]([C:9]1[CH:13]=[CH:14][C:6]([F:5])=[CH:7][CH:8]=1)=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 162513,4-DimethoxyphenolHCID 25135Boron TrichlorideHCID 678794-Fluorobenzoyl chloride

Product 1

HCID 54498197HCID 54498197, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A 1.0M solution of boron trichloride(142 ml) in dichioromethane was added to 4-fluorobenzoyl chloride(16.8 ml) in benzene (200 ml). Next, 3,4-dimethoxyphenol(20.0 g) in benzene (100 ml) was added and the reaction mixture was stirred at room temperature for 2 hours. The mixture was then poured onto ice water and allowed to stir for 15 minutes, then 1N HCl (500 ml) was added and stirred at room temperature for 17 hours. The reaction mixture was extracted with EtOAc, the EtOAc was separated, concentrated and dried to give the title product(41.7 g) as an orange solid. 1H NMR consistent with desired structures.

Workup

  1. additionThe mixture was then poured onto ice water
  2. stirringto stir for 15 minutes
  3. stirringstirred at room temperature for 17 hours
  4. extractionThe reaction mixture was extracted with EtOAc
  5. customthe EtOAc was separated
  6. concentrationconcentrated
  7. customdried

Sources & evidence

ORD record
ord-a073e857f9c1483a83003e64754d62f7
Source dataset
uspto-grants-1999_06
Patent number
US05910494

Reaction notes

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