Hydrochloric Acid → (4-Bromo-2-methoxyphenyl)(4-fluorophenyl)methanone

HRID 2116635

Reaction equation

HRID 2116635 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[F:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1.[Br:15][C:16]1[CH:17]=[C:18]([O:22][CH3:23])[CH:19]=[CH:20][CH:21]=1.Cl>ClCCCl>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([C:10]([C:9]2[CH:13]=[CH:14][C:6]([F:5])=[CH:7][CH:8]=2)=[O:11])=[C:18]([O:22][CH3:23])[CH:17]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 169713-BromoanisoleHCID 678794-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 59814869(4-Bromo-2-methoxyphenyl)(4-fluorophenyl)methanoneYield 18.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a suspension of AlCl3 (14.7 g, 110 mmol) in 250 mL of 1,2-dichloroethane was added 4-fluorobenzoyl chloride (11.8 mL, 100 mmol) at rt. The resulting mixture was stirred at rt for 15 min. and 3-bromoanisole (16.8 g, 90.0 mmol) in 20 mL of 1,2-dichloroethane was added. After 1 h at rt, the brown solution was poured into ice. 2N HCl was added to the aqueous layer followed by an extraction with CH2Cl2. The combined organics were dried (MgSO4), filtered and concentrated. The residue was subjected to chromatography on silica gel (EtOAc/hexane 5:95 to 7:93) affording 5.1 g of a solid that was triturated with 20 mL of EtOAc/hexane (10:90). The title compound was obtained from filtration, and additional product was recovered from the mother liquors.

Workup

  1. waitAfter 1 h at rt
  2. additionthe brown solution was poured into ice
  3. extractionfollowed by an extraction with CH2Cl2
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bc439dbf08e24a499e1b74945d71ca24
Source dataset
uspto-grants-2008_10
Patent number
US07439260B2

Linked notes

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