Benzyl Bromide → (E)-1-(3(benzyloxy)prop-1enyl)2-chlorobenzene

HRID 1506984Notes

Reaction equation

HRID 1506984 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[CH2:10][OH:11].[H-].[Na+].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([O:11][CH2:10]/[CH:9]=[CH:8]/[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 11557356(2E)-3-(2-Chlorophenyl)-2-propen-1-ol

Product 1

HCID 90033540(E)-1-(3(benzyloxy)prop-1enyl)2-chlorobenzeneYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (E)-3-(2-chlorophenyl) prop-2-en-1-ol(Preparation example 1, 5.3 g, 31.6 mmole) in THF was added NaH (60% in mineral oil, 0.91 g, 37.7 mmole) and Benzyl bromide (4.12 mL, 34.8 mmole), sequently at 0° C. The reaction mixture was stirred at room temperature for 18 hr. The TLC showed complete consumption of SM. The reaction mixture was quenched with H2O at 0° C. then extracted with EtOAc. The aqueous layer was extracted with EtOAc and separated. The combined organic layer was washed with H2O, then dried over MgSO4 and evaporated under reduced pressure. The crude compound was purified by silica ge column to produce the title compound (4.94 g, 70˜90%).

Workup

  1. customsequently at 0° C
  2. customconsumption of SM
  3. customThe reaction mixture was quenched with H2O at 0° C.
  4. extractionthen extracted with EtOAc
  5. extractionThe aqueous layer was extracted with EtOAc
  6. customseparated
  7. washThe combined organic layer was washed with H2O
  8. dry with materialdried over MgSO4
  9. customevaporated under reduced pressure
  10. customThe crude compound was purified by silica ge column

Sources & evidence

ORD record
ord-d3c51ccb2c9e43839281fb9c2096e137
Source dataset
uspto-grants-2015_12
Patent number
US09221783B2

Reaction notes

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