Water → 2-Bromo-1,3,5-trimethoxybenzene

HRID 2060347Notes

Reaction equation

HRID 2060347 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[CH:4]=1.[Br:13]Br.O>ClCCl>[Br:13][C:4]1[C:5]([O:11][CH3:12])=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 693011,3,5-Trimethoxybenzene

Product 1

HCID 708022-Bromo-1,3,5-trimethoxybenzeneYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

KM03 Dissolve 1,3,5-trimethoxybenzene (10.0 g, 59.46 mmol) in anhydrous dichloromethane (100 mL), cool the reaction mixture to −78° C., add dropwise bromine (3.0 mL, 59.44 mmol) stir the mixture for 1 h between −70° C. and −40° C. Warm up the solution to 0° C. and add water. Separate layers and extract the aqu. layer with EtAOc (3 times). Wash combined organic layer with water and brine and dry it with Na2SO4. Remove solvent and purify the crude product by recrystallization from hot EtOAc and cyclohexane to obtain 2-Bromo-1,3,5-trimethoxy-benzene (48) as a white solid (8.84 g, 60%). 1H NMR (400 MHz, CDCl3): 3.80 (s, 3H); 3.86 (s, 6H); 6.15 (s, 2H).

Workup

  1. extractionSeparate layers and extract the aqu
  2. washWash
  3. dry with materialdry it with Na2SO4
  4. customRemove solvent and purify the crude product
  5. customby recrystallization from hot EtOAc and cyclohexane

Sources & evidence

ORD record
ord-e84a5add29224cd386a6146af310c284
Source dataset
uspto-grants-2012_10
Patent number
US08278356B2

Reaction notes

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