Water → 3-(3-Bromopropoxy-4-methoxyphenyl)phenylmethanone

HRID 363559Notes

Reaction equation

HRID 363559 reaction equation
O[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9]C=1)=O.[H-].[Na+].[Br:20][CH2:21][CH2:22][CH2:23]Br.[OH2:25].CN(C)[CH:28]=[O:29]>>[Br:20][CH2:21][CH2:22][CH2:23][O:25][C:3]1[CH:2]=[C:15]([O:16][CH3:17])[CH:14]=[CH:13][C:4]=1[C:5]1[CH:7]=[C:12]([CH:28]=[O:29])[CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 41488933-Hydroxy-4-methoxybenzophenone

Product 1

HCID 219600893-(3-Bromopropoxy-4-methoxyphenyl)phenylmethanone

Conditions

Temperature
90 °C

Procedure

A solution of 3-hydroxy-4-methoxybenzophenone (4.6 g, 20 mmol) in dimethylformamide (35 ml) was treated with sodium hydride (600 mg, 25 mmol) at 0° C. for 20 minutes, then 1,3-dibromopropane (5 g, 24.7 mmol) was added in one portion. The mixture was heated at 90° C. for 1 hour, and then stirred at room temperature for 2 hours. At the end of the reaction, the mixture was poured into water (500 ml) and extracted with ethyl acetate (400 ml). The ethyl acetate solution was washed with water, brine and dried over anhydrous MgSO4. The solvent was removed and the crude oil was purified by flash chromatography over a silica gel column (SiO2, 85 g; eluted with 3:1 hexane: dichloromethane, 1.6 l; 3:7 hexane: dichloromethane, 1.4 l). The pure product thus obtained weighed 4.67 g, (66%) as an oil. Recrystallization twice from isopropyl ether (500 ml) gave analytically pure 3-(3-bromopropoxy-4-methoxyphenyl)phenylmethanone (2.42 g), m.p.=81°-83° C.

Workup

  1. customAt the end of the reaction
  2. extractionextracted with ethyl acetate (400 ml)
  3. washThe ethyl acetate solution was washed with water, brine
  4. dry with materialdried over anhydrous MgSO4
  5. customThe solvent was removed
  6. customthe crude oil was purified by flash chromatography over a silica gel column (SiO2, 85 g; eluted with 3:1 hexane: dichloromethane, 1.6 l; 3:7 hexane: dichloromethane, 1.4 l)
  7. customThe pure product thus obtained
  8. customRecrystallization twice from isopropyl ether (500 ml)

Sources & evidence

ORD record
ord-47a9c5f584db4a92abe7fc300ee0e501
Source dataset
uspto-grants-1999_02
Patent number
US05874435

Reaction notes

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