1-Bromo-4-fluorobenzene → HCID 21929393, compound

HRID 1243850Notes

Reaction equation

HRID 1243850 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.[CH3:10][O:11][CH2:12][C:13]([O:15]C)=O.[Cl-].[NH4+]>O1CCCC1>[F:9][C:6]1[CH:7]=[CH:8][C:3]([C:13]([C:3]2[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=2)([OH:15])[CH2:12][O:11][CH3:10])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 99931-Bromo-4-fluorobenzene2×HCID 25517Ammonium ChlorideHCID 80507Methyl methoxyacetateHCID 5462224Magnesium

Product 1

HCID 21929393HCID 21929393, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

4.9 g of magnesium, 5 cm3 of 4-bromofluorobenzene and 25 cm3 of tetrahydrofuran are heated to a temperature in the region of 60° C. 17 cm3 of 4-bromofluorobenzene in solution in 25 cm3 of tetrahydrofuran are added and the mixture is heated at a temperature in the region of 60° C. for 2 hours. 5 cm3 of methyl methoxyacetate in solution in 25 cm3 of tetrahydrofuran are added to the solution prepared above, cooled to a temperature in the region of 0° C. After stirring for 24 hours at a temperature in the region of 20° C., the reaction mixture is poured into 200 cm3 of saturated aqueous ammonium chloride solution and extracted with three times 75 cm3 of ethyl acetate, and the organic phases are washed with twice 100 cm3 of distilled water, dried over magnesium sulphate and concentrated to dryness under reduced pressure. The residue obtained is purified by flash chromatography on silica gel (35–70 μm), eluting with pure dichloromethane; 9.8 g of 1,1-bis(4-fluorophenyl)-2-methoxyethanol are thus obtained in the form of a yellow oil, the characteristics of which are as follows:

Workup

  1. customprepared above,
  2. temperaturecooled to a temperature in the region of 0° C
  3. extractionextracted with three times 75 cm3 of ethyl acetate
  4. washthe organic phases are washed with twice 100 cm3 of distilled water
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness under reduced pressure
  7. customThe residue obtained
  8. customis purified by flash chromatography on silica gel (35–70 μm)
  9. washeluting with pure dichloromethane

Sources & evidence

ORD record
ord-3c9ee98719d44da2a5e2ad737730080f
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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