1-Bromo-4-fluorobenzene → HCID 21929395, compound

HRID 1243847Notes

Reaction equation

HRID 1243847 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]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14].[Cl-].[NH4+]>O1CCCC1>[F:9][C:6]1[CH:7]=[CH:8][C:3]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([OH:14])[CH2:12][O:11][CH3:10])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 99931-Bromo-4-fluorobenzene2×HCID 25517Ammonium ChlorideHCID 776982-Methoxy-1-phenylethanoneHCID 5462224Magnesium

Product 1

HCID 21929395HCID 21929395, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

4.4 g of magnesium, 2 cm3 of 4-bromofluorobenzene and 10 cm3 of tetrahydrofuran are heated to a temperature in the region of 60° C. 18 cm3 of 4-bromofluorobenzene in solution in 50 cm3 of tetrahydrofuran are added and the mixture is heated at a temperature in the region of 60° C. for 2 hours. 8.4 cm3 of 2-methoxyacetophenone in solution in 60 cm3 of tetrahydrofuran are added to the solution prepared above, cooled to a temperature in the region of 5° 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 twice 150 cm3 of ethyl ether, and the organic phases are washed with twice 150 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 a cyclohexane/ethyl acetate (95/05) mixture; 13.2 g of 1-(4-fluorophenyl)-2-methoxy-1-phenylethanol are thus obtained in the form of a white oil, the characteristics of which are as follows:

Workup

  1. customprepared above,
  2. temperaturecooled to a temperature in the region of 5° C
  3. extractionextracted with twice 150 cm3 of ethyl ether
  4. washthe organic phases are washed with twice 150 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 a cyclohexane/ethyl acetate (95/05) mixture

Sources & evidence

ORD record
ord-c1df7f2bc38746dca6837273dc4884bc
Source dataset
uspto-grants-2006_10
Patent number
US07119115B2

Reaction notes

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