Sulfuric Acid → 3,5-Dibromoanisole

HRID 1035585Notes

Reaction equation

HRID 1035585 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Br:10])[C:3]=1N.S(=O)(=O)(O)O.O[PH2]=O.N([O-])=O.[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([Br:10])[CH:3]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 5428952,6-Dibromo-4-methoxyanilineHCID 4124402Phosphinic AcidHCID 23668193Sodium Nitrite

Product 1

HCID 110218123,5-DibromoanisoleYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2,6-dibromo-4-methoxyphenylamine (3 g, 10.67 mmol, 1 eq) in 10 ml of toluene cooled at 0° C. are added 6.6 ml of concentrated sulfuric acid and 17.5 ml of H3PO2 50% (15 eq). To the reaction mixture, sodium nitrite (1.47 mg, 21.35 mmol, 2 eq) is added, and all is stirred at 0° C. for 4.5 h. After neutralization with a sodium hydroxide solution, extraction with diethyl ether is performed. The organic phase is dried over magnesium sulfate, filtered and evaporated to dryness on a rotary evaporator. Purification of the raw product was not necessary (yield 96%, 2.7 g).

Workup

  1. extractionAfter neutralization with a sodium hydroxide solution, extraction with diethyl ether
  2. dry with materialThe organic phase is dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness on a rotary evaporator
  5. customPurification of the raw product

Sources & evidence

ORD record
ord-cff6d7a24ac14651af48d7279bdbe0f5
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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