2-Methyl-4-nitrophenol → 2-Bromo-6-methyl-4-nitrophenol

HRID 879266Notes

Reaction equation

HRID 879266 reaction equation
[Br:1]Br.[CH3:3][C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:13]>CC(O)=O>[Br:1][C:6]1[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=[C:4]([CH3:3])[C:5]=1[OH:13]

Participants

4

Reactant 2

HCID 74422-Methyl-4-nitrophenolHCID 24408Bromine

Product 1

HCID 203754122-Bromo-6-methyl-4-nitrophenolYield 80.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Br2 (122.2 g, 0.765 mol) was added into a solution of 2-methyl-4-nitrophenol (90.0 g, 0.588 mol) in HOAc (1.17 L) at room temperature. The resulting solution was stirred at room temperature for 4 h. TLC showed the reaction was complete. The solution was added into ice-water (3 L) slowly and filtered. The filter cake was dissolved into EA (2.5 L) and washed with saturated NaHSO3 (3×500 mL). The EtOAc layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford 2-bromo-6-methyl-4-nitrophenol (110 g, 80%) as yellow solid. 1H-NMR: 400 MHz, (CDCl3) δ: 8.30 (d, J=2.0 Hz, 1H), 8.05 (s, 1H), 6.22 (s, broad, 1H), 2.41 (s, 3H).

Workup

  1. filtrationfiltered
  2. dissolutionThe filter cake was dissolved into EA (2.5 L)
  3. washwashed with saturated NaHSO3 (3×500 mL)
  4. dry with materialThe EtOAc layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-549d83df6ae84ed9b2fc59d12efd3f3a
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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