Potassium Carbonate → 4-bromo-5-tert-butyl-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester

HRID 1481505ノート

反応式

HRID 1481505 の反応式
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:15])[N:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)=[O:5])[CH3:2].C([O-])([O-])=O.[K+].[K+].[Br:22]Br>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:15])[N:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:10]=1[Br:22])=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 24408BromineHCID 2799344ethyl 3-(tert-butyl)-1-methyl-1H-pyrazole-5-carboxylate

生成物 1

HCID 147933444-bromo-5-tert-butyl-2-methyl-2H-pyrazole-3-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 5-tert-butyl-2-methyl-pyrazole-3-carboxylic acid ethyl ester (2.00 g, 9.51 mmol) and K2CO3 (3.94 g, 28.5 mmol) in DCM (120 mL), in the dark, was added Br2 (1.46 mL, 28.5 mmol) slowly under Ar. After stirring at room temperature for 3 h under Ar, the resulting mixture was quenched with saturated aqueous Na2S2O3 (50 mL). The organic layer was separated and washed with H2O (50 mL) and brine (50 mL), then dried with Na2SO4. Removal of the solvent under reduced pressure yielded a white solid. 1H-NMR (400 MHz, CDCl3) δ: 4.40 (q, J=7.1 Hz, 2H), 4.08 (s, 3H), 1.43 (t, J=7.1 Hz, 3H), 1.42 (m, 9H). Mass Spectrum (LCMS, ESI pos.) Calculated For C11H17BrN2O2: 289.1 (M+H). Measured: 289.1.

後処理

  1. customthe resulting mixture was quenched with saturated aqueous Na2S2O3 (50 mL)
  2. customThe organic layer was separated
  3. washwashed with H2O (50 mL) and brine (50 mL)
  4. dry with materialdried with Na2SO4
  5. customRemoval of the solvent under reduced pressure
  6. customyielded a white solid

出典と根拠

ORDレコード
ord-eefa33a8d23f465faaa8d1f243cb3a45
出典データセット
uspto-grants-2016_08
特許番号
US09409915B2

反応ノート

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