Chloroform → tert-Butyl 5-bromonicotinate

HRID 545204ノート

反応式

HRID 545204 の反応式
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].CCN=C=N[CH2:16][CH2:17][CH2:18]N(C)C.[CH:22](Cl)(Cl)Cl>C(O)(C)(C)C.CN(C1C=CN=CC=1)C>[C:17]([O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[N:4][CH:5]=1)([CH3:18])([CH3:22])[CH3:16]

参加物

6

反応物 3

HCID 6212Chloroform2 回HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 887075-Bromonicotinic acid

生成物 1

HCID 18422124tert-Butyl 5-bromonicotinate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6386tert-Butanol溶媒

実験手順

5-Bromo-nicotinic acid (20.2 g, 100 mmol) was dissolved in CHCl3 (200 mL) and tert-BuOH (40 mL); and WSC (21.1 g, 110 mmol) and DMAP (21.1 g, 110 mmol) was added thereto in order, and stirred at room temperature over night. The reaction mixture was diluted with chloroform, washed with 0.5N HCl aq. (220 mL), 0.5N NaOH aq. (100 mL), brine and dried over MgSO4 and silica gel. After filtration, the solvents were removed in vacuo to afford 5-Bromo-nicotinic acid tert-butyl ester as a colorless solid. This solid was used for the next step without further purification.

後処理

  1. washwashed with 0.5N HCl aq. (220 mL), 0.5N NaOH aq. (100 mL), brine
  2. dry with materialdried over MgSO4 and silica gel
  3. filtrationAfter filtration
  4. customthe solvents were removed in vacuo

出典と根拠

ORDレコード
ord-f0d2641d1576477b8765ef3cd9aa53da
出典データセット
uspto-grants-2011_05
特許番号
US07935712B2

反応ノート

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