Bromine → HCID 19900785, compound

HRID 1029756Notes

Reaction equation

HRID 1029756 reaction equation
[Br:1]Br.[CH3:3][O:4][C:5]1[S:6][C:7]([S:10]([CH2:13][N+:14]([O-:16])=[O:15])(=[O:12])=[O:11])=[CH:8][CH:9]=1>C(O)(=O)C>[Br:1][C:9]1[CH:8]=[C:7]([S:10]([CH2:13][N+:14]([O-:16])=[O:15])(=[O:11])=[O:12])[S:6][C:5]=1[O:4][CH3:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 19900805HCID 19900805, compound

Product 1

HCID 19900785HCID 19900785, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (0.254 g) in acetic acid (2 ml) was added to a stirred solution of 2-methoxy-5-(nitromethylsulphonyl)thiophene (0.39 g) in acetic acid (8 ml). After 1hour the mixture was quenched with water (10 ml). The yellow precipitate was collected by filtration and recrystallised from ethanol to give 3-bromo-2-methoxy-5-(nitromethylsulphonyl)thiophene as a white solid (0.12 g) m.p. 120°-121° C.; m/e (electron impact): 315, 317 [mean M+ for Br=80 is 316]; NMR (90 MHz): 4.1 (s,3H), 5.60 (s,2H), 7.22 (s,1H); microanalysis, found: C,23.1; H,1.8; N,4.1%; C6H6BrNO5S2 requires C,22.8; H,1.9; N,4.4%.

Workup

  1. customAfter 1hour the mixture was quenched with water (10 ml)
  2. filtrationThe yellow precipitate was collected by filtration
  3. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-b9905f7a41704053b7a88a986484c4a0
Source dataset
uspto-grants-1992_04
Patent number
US05102905

Reaction notes

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