Benzyl Bromide → HCID 66875668, compound

HRID 1055597Notes

Reaction equation

HRID 1055597 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:16])=[C:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:7]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH2:17]([O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][C:6]2[CH:7]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=2[Cl:16])=[CH:10][CH:11]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 574237514-((5-Bromo-2-chlorophenyl)methyl)phenol

Product 1

HCID 66875668HCID 66875668, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[(5-bromo-2-chloro-phenyl)methyl]phenol 17b (2.0 g, 6.72 mmol, obtained from the synthetic method described in step 1 of example 17) and benzyl bromide (1.36 mL, 11.4 mmol) in tetrahydrofuran (20 mL) was added potassium carbonate (1.86 g, 13.4 mmol) at room temperature. The mixture was stirred at room temperature for 12 hours. The reaction mixture was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate (50 mL×3). The combined organic layers were washed with saturated aqueous sodium chloride (50 mL×2), dried over anhydrous sodium sulfate and filtered. The filtrated was concentrated in vacuo and the residue was purified by silica gel chromatography eluted with PE/EtOAc(v/v)=20/1 to give the title compound 25c as a white solid (1.83 g, 70.4%).

Workup

  1. customThe reaction mixture was quenched with saturated aqueous ammonium chloride
  2. extractionextracted with ethyl acetate (50 mL×3)
  3. washThe combined organic layers were washed with saturated aqueous sodium chloride (50 mL×2)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrated was concentrated in vacuo
  7. customthe residue was purified by silica gel chromatography
  8. washeluted with PE/EtOAc(v/v)=20/1

Sources & evidence

ORD record
ord-337ee6c7f15a4ca8b60fadfbd95a6bf6
Source dataset
uspto-grants-2016_07
Patent number
US09394329B2

Reaction notes

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