1-(4-(4-Bromophenoxy)phenyl)ethanone → 2-[4-(4-Bromo-phenoxy)-phenyl]-propan-2-ol

HRID 889642

Reaction equation

HRID 889642 reaction equation
[CH3:1][Mg]Br.[Br:4][C:5]1[CH:20]=[CH:19][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:18])[CH3:17])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1>C1COCC1>[Br:4][C:5]1[CH:20]=[CH:19][C:8]([O:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:18])([CH3:1])[CH3:17])=[CH:12][CH:11]=2)=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 108034801-(4-(4-Bromophenoxy)phenyl)ethanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 595717062-[4-(4-Bromo-phenoxy)-phenyl]-propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1.4 M solution of methylmagnesium bromide in THF (7.36 ml; 10.304 mmol) was added to a stirred solution of 4′-(4-bromophenoxy)acetophenone (1 g, 3.435 mmol; [CAS: 54916-27-7]) in THF (40 ml) at 0° C. under a nitrogen atmosphere. The reaction mixture was stirred for 3 hours. The reaction was quenched by the addition of an aqueous solution of saturated ammonium chloride and extracted with EtOAc. The combined organic extracts were dried (Na2SO4) and the solvent was evaporated to dryness. The crude residue was purified by column chromatography (silica gel; DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield intermediate D28 (0.8 g, 75%).

Workup

  1. customThe reaction was quenched by the addition of an aqueous solution of saturated ammonium chloride
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. customthe solvent was evaporated to dryness
  5. customThe crude residue was purified by column chromatography (silica gel; DCM as eluent)
  6. customThe desired fractions were collected
  7. customevaporated in vacuo
  8. customto yield intermediate D28 (0.8 g, 75%)

Sources & evidence

ORD record
ord-6ba909b9f17541058d2943e53f640a9d
Source dataset
uspto-grants-2012_08
Patent number
US08252937B2

Linked notes

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