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Hydrochloric Acid → (4-(2-Chloroethoxy)phenyl)(3-fluoro-4-methoxyphenyl)methanone

HRID 626144
Notes
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Reaction equation

HRID 626144 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5](Cl)=[O:6].[Al+3].[Cl-].[Cl-].[Cl-].[Cl:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl>ClCCl>[Cl:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:5]([C:4]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:2]([F:1])[CH:3]=2)=[O:6])=[CH:23][CH:22]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12156Benzene, (2-chloroethoxy)-HCID 27792553-Fluoro-4-methoxybenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 89656203(4-(2-Chloroethoxy)phenyl)(3-fluoro-4-methoxyphenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a solution of 3-fluoro-4-methoxybenzoyl chloride from the last step and anhydrous AlCl3 (1.30 g, 9.76 mmol) in dry dichloromethane (18 mL) was added (2-chloroethoxy)benzene (1.53 g, 9.76 mmol) in 2 mL dichloromethane at 0° C. After stirring at rt for 25 min, the mixture was poured into 3 N HCl. The mixture was extracted with dichloromethane. The extract was washed with sat. NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated to give the subtitle compound, which would be used for the next step directly.

Workup

  1. extractionThe mixture was extracted with dichloromethane
  2. washThe extract was washed with sat. NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c756a8092d5f4cbbbcfb12df486ac58f
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09309211B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes