1-Bromo-3-chloropropane → 4'-Chloro-4-chloropropoxybenzophenone

HRID 1613266Notes

Reaction equation

HRID 1613266 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:6][CH:5]=1.Br[CH2:20][CH2:21][CH2:22][Cl:23]>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10](=[O:18])[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:20][CH2:21][CH2:22][Cl:23])=[CH:13][CH:12]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 1235044-Hydroxy-4'-chlorobenzophenone

Product 1

HCID 537387314'-Chloro-4-chloropropoxybenzophenoneYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60%, 1.7 g, 43 mmol) in dimethylformamide (200 mL) was added 4'-chloro-4-hydroxybenzophenone (5 g, 22 mmol) portionwise. The mixture was stirred at room temperature for 2 hours, then 1-bromo-3-chloropropane (4.4 mL, 43 mmol) was added, and the mixture was stirred at room temperature overnight. The reaction was quenched with methanol (10 mL) and filtered through Celite®. The filtrate was taken up in ether (300 mL), washed thrice with water (150 mL) and dried over sodium sulfate. The solution was concentrated to give 6.1 g (90%) of 4'-chloro-4-chloropropoxybenzophenone as an amber oil. 1H NMR (CDCl3): δ7.98-6.89(m,8H), 4.19(t,2H), 3.85(t,2H), 2.29(m,2H).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe reaction was quenched with methanol (10 mL)
  3. filtrationfiltered through Celite®
  4. washwashed thrice with water (150 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-1f30335a37354733a0126542b33d5d9d
Source dataset
uspto-grants-1993_03
Patent number
US05192786

Reaction notes

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