Bromine → HCID 20231438, compound

HRID 2290557Notes

Reaction equation

HRID 2290557 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1.[Br:17]Br.S([O-])([O-])=O.[Na+].[Na+]>C(OCC)C.O1CCOCC1>[Br:17][C:14]1[S:13][C:12]([C:4]2[CH:5]=[CH:6][C:7]([N+:9]([O-:11])=[O:10])=[CH:8][C:3]=2[O:2][CH3:1])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 24408BromineHCID 24437Sodium SulfiteHCID 13768627Thiophene, 2-(2-methoxy-4-nitrophenyl)-

Product 1

HCID 20231438HCID 20231438, compoundYield 90.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a stirred 0° C. mixture of 8.0 g (0.034 mole) of 2-(2-methoxy-4-nitrophenyl)thiophene (Example 4, Step A) in 180 ml of diethyl ether was added a mixture of 10.8 g (0.07 mole) of bromine in 15.0 ml of 1,4-dioxane and 20 ml of diethyl ether. The mixture was allowed to warm to room temperature and stir for approximately 18 hours. The reaction mixture was poured into a mixture of sodium sulfite and ice water. The resultant mixture was extracted with diethyl ether, and the extract dried over anhydrous sodium sulfate. The dried extract was filtered, and the solvent evaporated from the filtrate to leave a residue. The residue was purified by column chromatography using silica gel and eluting with toluene to yield 9.7 g of 2-bromo-5-(2-methoxy-4-nitrophenyl)thiophene.

Workup

  1. additionwas added
  2. extractionThe resultant mixture was extracted with diethyl ether
  3. dry with materialthe extract dried over anhydrous sodium sulfate
  4. extractionThe dried extract
  5. filtrationwas filtered
  6. customthe solvent evaporated from the filtrate
  7. customto leave a residue
  8. customThe residue was purified by column chromatography
  9. washeluting with toluene

Sources & evidence

ORD record
ord-9c71a027f3f544d6a3cfe3aa4da726ad
Source dataset
uspto-grants-1986_10
Patent number
US04617316

Reaction notes

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