Hydrochloric Acid → 4-(4-Bromo-2,3-difluorophenyl)-2-methylnicotinic acid

HRID 1398372ノート

反応式

HRID 1398372 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16]C)=[O:15])=[C:12]([CH3:18])[N:11]=[CH:10][CH:9]=2)=[C:4]([F:19])[C:3]=1[F:20].[OH-].[Na+].Cl>CO.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([OH:16])=[O:15])=[C:12]([CH3:18])[N:11]=[CH:10][CH:9]=2)=[C:4]([F:19])[C:3]=1[F:20]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86710363Methyl 4-(4-bromo-2,3-difluorophenyl)-2-methylnicotinate

生成物 1

HCID 867103644-(4-Bromo-2,3-difluorophenyl)-2-methylnicotinic acid収率 91.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of methyl 4-(4-bromo-2,3-difluorophenyl)-2-methylnicotinate (800 mg, 2.34 mmol) in MeOH (10 mL) was added NaOH (935 mg, 23.38 mmol) in Water (10 mL). The reaction mixture was stirred at room temperature for 16 hrs. The reaction mixture was evaporated under reduced pressure and the residue obtained was adjusted to pH ˜3 by adding 1.5N HCl solution. The product was extracted with dichloromethane and the layers were separated. The organic phase was dried over Na2SO4, and concentrated under reduced pressure to afford 4-(4-bromo-2,3-difluorophenyl)-2-methylnicotinic acid (700 mg, 2.133 mmol, 91% crude yield) as an off-white solid which was carried on without further purification. LC/MS (ESI) m/e 330.0 [(M+2H)+, calcd for C13H10BrF2NO2 330.1]; LC/MS retention time (method C): tR=1.34 min.

後処理

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customthe residue obtained
  3. extractionThe product was extracted with dichloromethane
  4. customthe layers were separated
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-9fc3f6cdbf5d41e09719704f1e552538
出典データセット
uspto-grants-2014_12
特許番号
US08901305B2

反応ノート

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