1-Bromo-4-fluorobenzene → HCID 15737986, compound

HRID 728566Notes

Reaction equation

HRID 728566 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([Mg]Br)=[CH:4][CH:3]=1.BrC1C=CC(F)=CC=1.[Mg].[C:19]([C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=2)=[CH:24][CH:23]=1)(=[O:21])[CH3:20].[Cl-].[NH4+]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:19]([C:22]2[CH:23]=[CH:24][C:25]([C:28]3[CH:29]=[CH:30][N:31]=[CH:32][CH:33]=3)=[CH:26][CH:27]=2)([OH:21])[CH3:20])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 99931-Bromo-4-fluorobenzeneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 149886961-[4-(4-Pyridinyl)phenyl]-ethanoneHCID 178418676HCID 178418676, compound

Product 1

HCID 15737986HCID 15737986, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-fluorophenylmagnesium bromide (prepared from 7.6 ml (0.070 mol) 4-bromofluorobenzene and 3.40 g (0.14 mol) magnesium turnings) in tetrahydrofuran (150 mL) was added to a suspension of 4-(4-acetylphenyl)pyridine (9.85 g, 0.050 mol) in tetrahydrofuran (50 mL) at 0°. The mixture was stirred for 30 min at 0° and for 30 min at room temperature, then was poured into saturated aqueous ammonium chloride. The mixture was extracted with ether, the organic phase was washed with water and brine, then was dried over magnesium sulfate and concentrated. The residue was recrystallized (1-chlorobutane) to give 1-(4-fluorophenyl)-1-[4-(4-pyridyl)phenyl]ethanol colorless needles (10.0 g, 68%). MP 166-170°; NMR (CDCl3) 8.60 (d, 2H), 7.60-7.40 (8H), 7.00 (t, 2H), 2.00 (s, 3H).

Workup

  1. extractionThe mixture was extracted with ether
  2. washthe organic phase was washed with water and brine
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was recrystallized (1-chlorobutane)

Sources & evidence

ORD record
ord-1e747329984940c5bf87c657f40a67d2
Source dataset
uspto-grants-1991_09
Patent number
US05049570

Reaction notes

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