Diethyl Ether → Methyl 6-bromo-3-hydroxypicolinate

HRID 277143

反応式

HRID 277143 の反応式
[OH:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[Br:12]Br.CCOCC>O>[Br:12][C:5]1[N:4]=[C:3]([C:8]([O:10][CH3:11])=[O:9])[C:2]([OH:1])=[CH:7][CH:6]=1

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 24408BromineHCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylate

生成物 1

HCID 22175135Methyl 6-bromo-3-hydroxypicolinate収率 70.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mechanically stirred solution of methyl 3-hydroxypicolinate (30.6 g) in water (800 mL) was slowly added bromine (32 g) over a 30 minute period. After the addition was complete, stirring was continued for an additional hour. Ether (300 mL) was added and stirring continued until all the solids had dissolved. The organic layer was separated and the aqueous phase extracted with ether (200 mL). The organic phases were combined, dried (MgSO4) and the solvent evaporated to give 32.8 g of methyl 6-bromo-3-hydroxypicolinate as an off-white solid. Recrystallization from methanol/water gave an analytical sample, m.p. 115-117° C.

後処理

  1. customover a 30 minute
  2. additionAfter the addition
  3. waitwas continued for an additional hour
  4. stirringstirring
  5. dissolutionhad dissolved
  6. customThe organic layer was separated
  7. extractionthe aqueous phase extracted with ether (200 mL)
  8. dry with materialdried (MgSO4)
  9. customthe solvent evaporated

出典と根拠

ORDレコード
ord-a67842e8f30145169cc0716f478f3f78
出典データセット
uspto-grants-2002_03
特許番号
US06355660B1

関連ノート

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