Potassium Carbonate → 1-Bromo-2-(2,4-difluorophenoxy)-4-methyl-5-nitrobenzene

HRID 912443Notes

Reaction equation

HRID 912443 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH3:11])=[CH:4][C:3]=1Br.[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[OH:21].C([O-])([O-])=O.[K+].[K+]>>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([CH3:11])=[CH:4][C:3]=1[O:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[F:13]

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 1230512,4-DifluorophenolHCID 574187581,2-Dibromo-4-methyl-5-nitrobenzene

Product 1

HCID 574187591-Bromo-2-(2,4-difluorophenoxy)-4-methyl-5-nitrobenzeneYield 95%

Conditions

Temperature
100 °C

Procedure

A mixture of 1,2-dibromo-4-methyl-5-nitrobenzene (84.3 g, 286 mmol), 2,4-difluorophenol (37.2 g, 286 mmol), and K2CO3 (43.5 g, 315 mmol) were heated to 100° C. for 45 hours. The reaction mixture was cooled to room temperature and then stored in a 5° C. refrigerator overnight. The reaction mixture was poured into 1200 mL of ice water. The resulting damp solid was collected, partially ground up, and stirred in 900 mL H2O for 45 minutes. The solid was collected by filtration and rinsed with 700 mL of water portion-wise. The resulting solid was dried under high vacuum overnight to yield 93.5 g of the desired product as a brown solid (95% yield). 1H NMR (400 MHz, CDCl3) δ 8.38 (s, 1H), 7.18 (m, 1H), 7.03 (m, 1H), 6.97 (m, 1H), 6.52 (s, 1H), 2.50 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customstored in a 5° C.
  3. customrefrigerator overnight
  4. customThe resulting damp solid was collected
  5. filtrationThe solid was collected by filtration
  6. washrinsed with 700 mL of water portion-wise
  7. customThe resulting solid was dried under high vacuum overnight

Sources & evidence

ORD record
ord-d0c668d9778d4ee9a0a5430bcebed601
Source dataset
uspto-grants-2011_09
Patent number
US08026233B2

Reaction notes

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