Bromine → 2-Bromo-1-(4'-bromo-1,1'-biphenyl-4-yl)ethanone

HRID 1625490

Reaction equation

HRID 1625490 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Br:17]Br>C(Cl)Cl>[Br:17][CH2:15][C:14]([C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)=[O:16]

Participants

4

Reactant 2

HCID 24408BromineHCID 798061-(4'-Bromo(1,1'-biphenyl)-4-yl)ethan-1-one

Product 1

HCID 32747482-Bromo-1-(4'-bromo-1,1'-biphenyl-4-yl)ethanoneYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-[4-(4-bromophenyl)phenyl]ethanone (5 g, 18.17 mmol) in CH2Cl2 (40 mL) is added bromine (983 μL, 19 mmol). The resulting mixture is stirred for 48 hours at room temperature. The mixture is diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate, water, brine, dried over anhydrous sodium sulfate and concentrated. The crude solid is triturated with ether to give 2-bromo-1-[4-(4-bromophenyl)phenyl]ethanone (5.7 g, 88.6%) as a white solid.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate, water, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe crude solid is triturated with ether

Sources & evidence

ORD record
ord-56e3e94580c14036b2fa6cd417fff457
Source dataset
uspto-grants-2014_07
Patent number
US08779156B2

Linked notes

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