Methanol → 2-Methoxy-2'-nitro-4,4'-dibromobiphenyl

HRID 565591Notes

Reaction equation

HRID 565591 reaction equation
[CH3:1][O-:2].[Na+].CO.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=2[N+:20]([O-:22])=[O:21])=[C:9]([N+]([O-])=O)[CH:8]=1>CN(C=O)C>[CH3:1][O:2][C:9]1[CH:8]=[C:7]([Br:6])[CH:12]=[CH:11][C:10]=1[C:13]1[CH:18]=[CH:17][C:16]([Br:19])=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21]

Participants

5

Reactant 3

HCID 887MethanolHCID 100466484,4'-Dibromo-2,2'-dinitro-1,1'-biphenylHCID 10942334Sodium Methoxide

Product 1

HCID 99774712-Methoxy-2'-nitro-4,4'-dibromobiphenylYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of sodium methoxide in methanol (22.7 mL, 99.4 mmol) was added dropwise to a solution of 4,4′-dibromo-2,2′-dinitrobiphenyl (14, 33.28 g, 82.79 mmol) in DMF (250 mL) cooled in ice-bath. The reaction mixture was stirred overnight at room temperature under N2. The reaction mixture was then poured into ice-water (700 mL). The precipitated solid was collected and recrystallized from acetonitrile (200 mL) and methanol (100 mL) to give an olive green crystal (18.88 g, 59.0%): mp 127-129° C.; HPLC method 3 tR=9.57 min (96.5 area %); 1H NMR (400 MHz, CDCl3) δ 3.69 (s, 3 H), 7.04 (d, J=1.6 Hz, 1 H), 7.14 (d, J=8.1 Hz, 1 H), 7.23 (dd, J1=1.6 Hz, J2=7.3 Hz, 1 H), 7.26 (d, J=7.3 Hz, 1 H), 7.76 (dd, J1=1.9 Hz, J2=8.1 Hz, 1 H), 8.09 (d, J=1.9 Hz, 1 H); EI-MS m/z 385 (M+). Anal. (C13H9O3NBr2) C, H, N.

Workup

  1. temperaturecooled in ice-bath
  2. customThe precipitated solid was collected
  3. customrecrystallized from acetonitrile (200 mL) and methanol (100 mL)

Sources & evidence

ORD record
ord-42e49a71da8a4d8a8aa56ff7859972f8
Source dataset
uspto-grants-2001_01
Patent number
US06172104B2

Reaction notes

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