Nitric Acid → 3-Bromo-2-nitro-benzo(b)thiophene

HRID 2174145

Reaction equation

HRID 2174145 reaction equation
[Br:1][C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1.[N+:11]([O-])([OH:13])=[O:12]>C(O)(=O)C>[Br:1][C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[S:5][C:6]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 123250Benzo(b)thiophene, 3-bromo-

Product 1

HCID 2970503-Bromo-2-nitro-benzo(b)thiopheneYield 72%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Into a solution of 3-bromobenzo[b]thiophene (40 g, 190 mmol) in glacial acetic acid (140 ml) was added a solution of nitric acid (74 ml, 1760 mmol) in glacial acetic acid (40 mL) over a period of 45 min. The reaction mixture was stirred at room temperature for 5 hours before quenching with water. The precipitate was isolated by filtration, washed with water and recrystallized from ethyl acetate/hexane (1/1, v/v) to yield 3-bromo-2-nitrobenzo[b]thiophene (35 g, 72%) as yellow crystals.

Workup

  1. custombefore quenching with water
  2. customThe precipitate was isolated by filtration
  3. washwashed with water
  4. customrecrystallized from ethyl acetate/hexane (1/1

Sources & evidence

ORD record
ord-ac3ad3688ca549dca5a572b7ccefd7bf
Source dataset
uspto-grants-2015_06
Patent number
US09059412B2

Linked notes

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