Bromine → 2-Bromo-1-(2,2-diphenyl-benzo(1,3)dioxol-5-yl)-propan-1-one

HRID 1384329Notes

Reaction equation

HRID 1384329 reaction equation
[C:1]1([C:7]2([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:11][C:10]3[CH:12]=[CH:13][C:14]([C:16](=[O:19])[CH2:17][CH3:18])=[CH:15][C:9]=3[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:26]Br>C(Cl)(Cl)(Cl)Cl>[Br:26][CH:17]([CH3:18])[C:16]([C:14]1[CH:13]=[CH:12][C:10]2[O:11][C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[O:8][C:9]=2[CH:15]=1)=[O:19]

Participants

4

Reactant 2

HCID 24408BromineHCID 211866231-(2,2-Diphenyl-benzo(1,3)dioxol-5-yl)-propan-1-one

Product 1

HCID 222257572-Bromo-1-(2,2-diphenyl-benzo(1,3)dioxol-5-yl)-propan-1-oneYield 96%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1-(2,2-Diphenyl-benzo(1,3)dioxol-5-yl)-propan-1-one (the compound of Preparation 42, 4.70 g, 14.23 mmol) was dissolved in carbon tetrachloride (60 mL) and bromine (0.74 mL, 14.36 mmol in 10 mL of carbon tetrachloride) was added dropwise. The reaction was stirred at ambient temperature 30 min and then it was extracted with saturated aqueous bicarbonate solution. The organic phase was washed with water and brine, dried over magnesium sulfate, and concentrated to afford 5.58 g (96%) of 2-bromo-1-(2,2-diphenyl-benzo(1,3)dioxol-5-yl)-propan-1-one as a dark orange oil which had: NMR δ7.68-7.37 (m, 12 H), 6.95 (d, J=8.3 Hz, 1 H), 5.21 (q, J=6.7 Hz, 1 H), 1.88 (d, J=6.6 Hz, 3 H).

Workup

  1. extractionit was extracted with saturated aqueous bicarbonate solution
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1d9019f8ac8d42e7a0ede2010b41e1d2
Source dataset
uspto-grants-2001_07
Patent number
US06258827B1

Reaction notes

Loading…