Bis(3-bromophenyl)methanol → Bis(3-bromophenyl)methanone

HRID 1429268Notes

Reaction equation

HRID 1429268 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[CH:11]=2)[OH:9])[CH:5]=[CH:6][CH:7]=1>ClCCl.O=[Mn]=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Br:16])[CH:11]=2)=[O:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 21620630Bis(3-bromophenyl)methanol

Product 1

HCID 12731928Bis(3-bromophenyl)methanoneYield 91%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

MnO2 (21.61 g, 249 mmol) was added to a solution of bis(3-bromophenyl)methanol (8.4 g, 24.5 mmol) in dichloromethane (80 mL). The mixture was stirred at 25° C. for 12 h and then filtered. The filter cake was washed with dichloromethane (60 mL×5). The filtrate was concentrated to afford 7.6 g of the title compound (22.3 mmol, 90%). LC/MS: [M+1]=341. 1H NMR (DMSO-d6), 400 MHz: δ 7.52-7.56 (m, 2H), 7.71 (d, 2H, J=7.2 Hz), 7.88-7.92 (m, 4H).

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with dichloromethane (60 mL×5)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-da04784e106f48c4aeea7450e89e3e74
Source dataset
uspto-grants-2015_01
Patent number
US08937150B2

Reaction notes

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