Bromine → 1-(Bromomethyl)-4-(4-nitrophenoxy)benzene

HRID 1065280Notes

Reaction equation

HRID 1065280 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[Br:18]Br>C(Cl)(Cl)(Cl)Cl>[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][Br:18])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 769431-Methyl-4-(4-nitrophenoxy)benzene

Product 1

HCID 205403221-(Bromomethyl)-4-(4-nitrophenoxy)benzene

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a refluxing (250 watt infra-red lamp) and stirred solution of 4-(4-nitrophenoxy)toluene (229.25 g; 1 mol) in CCl4 (2.5 l) under nitrogen, bromine (247.46 g; 1.55 mol) in CCl4 (250 ml) was added dropwise over a period of 4 hours. After refluxing an additional 8 hours, followed by stirring at room temperature overnight, the reaction mixture was washed with 10% sodium bisulphite (1×1 l), saturated sodium bicarbonate (2×2 l) and saturated sodium chloride. The organic layer was dried over magnesium sulphate and evaporated to give a yellow solid which was recrystallised from benzene-hexane (250 ml:350 ml) to yield 4-(4-nitrophenoxy)α-bromotoluene as light yellow crystals. m.p. 68°-70° C. NMR (CDCl3): 8.15 (d,2H), 7.45 (d,2H), 7.0 (d,4H); and 4.49 (s,2H). Analysis: calculated for C13H10BrNO3 : C, 50.67; H, 3.27; N, 4.55; Br, 25.93; found: C, 50.38; H, 3.24; N, 4.58; Br, 26.02.

Workup

  1. temperatureAfter refluxing an additional 8 hours
  2. washthe reaction mixture was washed with 10% sodium bisulphite (1×1 l), saturated sodium bicarbonate (2×2 l) and saturated sodium chloride
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. customevaporated
  5. customto give a yellow solid which
  6. customwas recrystallised from benzene-hexane (250 ml:350 ml)

Sources & evidence

ORD record
ord-4ee131bafcd441cbb39f3734d623adb4
Source dataset
uspto-grants-1982_05
Patent number
US04329365

Reaction notes

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