Bromine → 1-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one

HRID 1422064Notes

Reaction equation

HRID 1422064 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)=[O:3].[Br:18]Br>CO>[CH2:11]([O:10][C:7]1[CH:8]=[CH:9][C:4]([C:2](=[O:3])[CH2:1][Br:18])=[CH:5][CH:6]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-one

Product 1

HCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-oneYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

4-Benzyloxyacetophenone (56.57 g, 250 mmol) was dissoved in 1350 ml of methanol, with warming, and bromine (15.5 ml, 300 mmol) was added dropwise as a solution in 150 ml of methanol. After stirring for 3 hours the methanol was evaporated and the residue was suspended in 200 ml of 1 M hydrochloric acid and stirred for 10 minutes. The organic material was extracted into dichloromethane (1×500 ml, and 1×200 ml). The combined organic layers were washed with brine, dried over magnesium sulfate, and evaporated to an off-white solid, which was recrystalized from hot ethanol and water, to afford 69.39 g (91%) of 4-benzyloxyphenacylbromide. M.p. 85-88° C. MS(GC): m/z 306 (M+1). 1H-NMR (CDCl3, 200 MHz) δ: 4.39 (s, 2H); 5.13 (s, 2H); 7.03 (d, 2H); 7.32-7.46 (m, 5H); 7.98 (d, 2H).

Workup

  1. temperaturewith warming
  2. customwas evaporated
  3. extractionThe organic material was extracted into dichloromethane (1×500 ml, and 1×200 ml)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to an off-white solid, which
  7. customwas recrystalized from hot ethanol and water

Sources & evidence

ORD record
ord-4255e6f73bd940818b212e0d26251b12
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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