Lithium Hydroxide → HCID 86695927, 화합물

HRID 1398452노트

반응식

HRID 1398452 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([O:16]C)=[O:15])=[CH:12][N:11]=[CH:10][C:9]=2[F:18])=[C:4]([F:19])[CH:3]=1.[Li+].[OH-]>O1CCCC1.CO.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][N:11]=[CH:10][C:9]=2[F:18])=[C:4]([F:19])[CH:3]=1

참가 물질

6

반응물 2

HCID 3939Lithium HydroxideHCID 86695924HCID 86695924, 화합물

생성물 1

HCID 86695927HCID 86695927, 화합물수율 93%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To the solution of methyl 4-(4-chloro-2-fluorophenyl)-5-fluoronicotinate (600 mg, 2.115 mmol) in tetrahydrofuran (2.5 mL), MeOH (2.5 mL) and water (2.5 mL) was added LiOH (50.7 mg, 2.115 mmol) and the mixture was stirred at rt for 12 h. The volatiles were removed and the residue was diluted with water. The pH was adjusted to 4 with 1.5N HCl. The product was extracted with ethyl acetate (2×5 mL). The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to afford 4-(4-chloro-2-fluorophenyl)-5-fluoronicotinic acid (530 mg, 1.966 mmol, 93% crude yield) the pale brown solid. The material was carried on without further purification. LC/MS (ESI) m/e 269.9 [(M+H)+, calcd for C12H7ClF2NO2 270.0]; LC/MS retention time (method D): tR=0.88 min.

후처리

  1. customThe volatiles were removed
  2. additionthe residue was diluted with water
  3. extractionThe product was extracted with ethyl acetate (2×5 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-68d86f3518084c6286f6ba71ddca8030
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901305B2

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