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

HRID 1383563Notes

Reaction equation

HRID 1383563 reaction equation
[Br:1]Br.[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(Cl)(Cl)Cl>[Br:1][CH2:18][C:17]([C:14]1[CH:13]=[CH:12][C:11]([O:10][CH2:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:16][CH:15]=1)=[O:19]

Participants

4

Reactant 2

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

Product 1

HCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bromine (80 mmol) was added dropwise over 5 min to a stirred solution of 4′-benzyloxyacetophenone (70 mmol) in 40 ml chloroform. This mixture was stirred for an additional 5 min and quenched with saturated sodium bicarbonate in water until the pH reached 7. The organic layers were combined, dried over MgSO4, and concentrated to dryness. The crude mixture was purified over a silica gel column and eluted with methylene chloride to yield 2-bromo-4′-benyloxyacetophenone. An Rf of 0.62 was observed when resolved by thin layer chromatography using methylene chloride. 1H nmr (δ, ppm, CDCl3), 7.97 (2H, δ, 9.2 Hz, O—Ar—C(O)), 7.43 (5H, m, Ar′CH2O—), 7.04 (2H, δ, 9.0 Hz, O—Ar—C(O)), 5.15 (2H, s, Ar′CH2O—), 4.40 (2H, s, CH2Br).

Workup

  1. customquenched with saturated sodium bicarbonate in water until the pH
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated to dryness
  4. customThe crude mixture was purified over a silica gel column
  5. washeluted with methylene chloride

Sources & evidence

ORD record
ord-cbe4c4e3701445d19b89f8cac9d65cd1
Source dataset
uspto-grants-2001_07
Patent number
US06255336B1

Reaction notes

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