Hydrochloric Acid → (4-(2-Bromoethoxy)-3-fluorophenyl)(4-methoxyphenyl)methanone

HRID 626134Notes

Reaction equation

HRID 626134 reaction equation
[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][C:6]=1[F:14].[Al+3].[Cl-].[Cl-].[Cl-].[C:19]1([O:25][CH3:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>ClCCl>[Br:1][CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([C:22]2[CH:23]=[CH:24][C:19]([O:25][CH3:26])=[CH:20][CH:21]=2)=[O:10])=[CH:7][C:6]=1[F:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7519AnisoleHCID 6451240Aluminum(III) ChlorideHCID 896561284-(2-Bromoethoxy)-3-fluorobenzoyl chloride

Product 1

HCID 89656419(4-(2-Bromoethoxy)-3-fluorophenyl)(4-methoxyphenyl)methanoneYield 78.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-(2-bromoethoxy)-3-fluorobenzoyl chloride (1.07 g, 3.80 mmol) and anhydrous AlCl3 (1.01 g, 7.60 mmol) in dry dichloromethane (18 mL) was added anisole (822 mg, 7.60 mmol) in 2 mL dichloromethane at 0° C. After stirring at rt for 6 h, the mixture was poured into 3 N HCl and extracted with dichloromethane twice. The extracts were combined, washed with sat. NaHCO3 and brine, dried over Na2SO4, filtered, concentrated, and purified by column chromatography over silica gel (eluent: petroleum ether/ethyl acetate=10/1 to 5/1) to give 1.05 g (77% yield) of the subtitle compound as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.79 (d, J=8.8 Hz, 2H), 7.58 (d, J=11.6 Hz, 1H), 7.55 (d, J=8.4 Hz, 1H), 7.03 (dd, J=8.0 Hz, 8.4 Hz, 1H), 6.98 (d, J=9.2 Hz, 2H), 4.44 (t, J=6.4 Hz, 2H), 3.90 (s, 3H), 3.70 (t, J=6.4 Hz, 2H).

Workup

  1. extractionextracted with dichloromethane twice
  2. washwashed with sat. NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography over silica gel (eluent: petroleum ether/ethyl acetate=10/1 to 5/1)

Sources & evidence

ORD record
ord-211ef298468f4959af4a512b0b33a96f
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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