N-bromobutanimide → HCID 57826909, compound

HRID 2392095Notes

Reaction equation

HRID 2392095 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([C:15]([O:17][CH3:18])=[O:16])[S:10][C:11]=2[CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=[N:3]1.[Br:19]N1C(=O)CCC1=O>O1CCCC1>[Br:19][C:5]1[CH:4]=[N:3][N:2]([CH3:1])[C:6]=1[C:7]1[CH:8]=[C:9]([C:15]([O:17][CH3:18])=[O:16])[S:10][C:11]=1[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 57826920HCID 57826920, compound

Product 1

HCID 57826909HCID 57826909, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 4-(1-methyl-1H-pyrazol-5-yl)-5-propyl-2-thiophenecarboxylate (714 mg, 2.70 mmol) and N-bromosuccinimide (481 mg, 2.70 mmol) in tetrahydrofuran (12 ml) was stirred in a sealed tube for 1 h at 70° C. The reaction mixture was divided and half was partitioned between H2O-DCM. The aqueous phase was washed several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and used directly yielding methyl 4-(4-bromo-1-methyl-1H-pyrazol-5-yl)-5-propyl-2-thiophenecarboxylate (464 mg, 1.35 mmol, 50% yield) as an orange oil: LCMS (ES) m/e 343, 345 (M, M+2)+.

Workup

  1. customhalf was partitioned between H2O-DCM
  2. washThe aqueous phase was washed several times with DCM
  3. dry with materialthe combined organic fractions were dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9ea4fdfcc4b94a60a947cdc9d637a683
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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