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

HRID 413823Notes

Reaction equation

HRID 413823 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:18]Br>C(Cl)(Cl)Cl>[Br:18][CH2:16][C:15]([C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1)=[O:17]

Participants

4

Reactant 2

HCID 24408BromineHCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-one2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Bromination of 4′-benzyloxyacetophenone (step 2): 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-4fbf97930fc94f20b8adfd5a4601f600
Source dataset
uspto-grants-2003_05
Patent number
US06569889B2

Reaction notes

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