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

HRID 1003633Notes

Reaction equation

HRID 1003633 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 δ 7.68-7.37 (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-d03a7cb0c28949be81a0b29735bee791
Source dataset
uspto-grants-2000_04
Patent number
US06046213

Reaction notes

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