Ethanone, 1-(3,5-bis(phenylmethoxy)phenyl)- → 1-(3,5-Bis(phenylmethoxy)phenyl)-2-bromoethan-1-one

HRID 494417Notes

Reaction equation

HRID 494417 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C:23](=[O:25])[CH3:24])[CH:12]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-:26].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.CO>[CH2:16]([O:15][C:13]1[CH:12]=[C:11]([C:23](=[O:25])[CH2:24][Br:26])[CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:14]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 120098Ethanone, 1-(3,5-bis(phenylmethoxy)phenyl)-HCID 23500184Tetra-n-butylammonium tribromide

Product 1

HCID 1200971-(3,5-Bis(phenylmethoxy)phenyl)-2-bromoethan-1-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1-[3,5-bis(benzyloxy)phenyl]ethanone (5 g, 15.04 mmol) in tetrahydrofuran (60 mL) and methanol (35 mL) was added tetrabutylammonium tribromide (7.25 g, 15.04 mmol) in tetrahydrofuran (20 mL) at room temperature. The reaction mixture was stirred for 24 hours and the solvent removed in vacuo. The residue was dissolved in ethyl acetate (100 mL) and washed with water (2×50 mL). The combined organic extracts were dried over magnesium sulfate and concentrated to afford the desired compound as a yellow oil in quantitative yield.

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (100 mL)
  3. washwashed with water (2×50 mL)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-37b82bc9545047b0916a4cec67c3ded1
Source dataset
uspto-grants-2009_05
Patent number
US07538141B2

Reaction notes

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