2-Chloroaniline → 5-Bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid

HRID 494684

반응식

HRID 494684 반응식
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[NH2:18].[Br:19][C:20]1[C:21]([F:31])=[C:22]([F:30])[C:23](F)=[C:24]([CH:28]=1)[C:25]([OH:27])=[O:26]>C1COCC1>[Br:19][C:20]1[C:21]([F:31])=[C:22]([F:30])[C:23]([NH:18][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[Cl:11])=[C:24]([CH:28]=1)[C:25]([OH:27])=[O:26]

참가 물질

5

반응물 3

HCID 72402-ChloroanilineHCID 2733832Lithium HexamethyldisilazideHCID 111186375-Bromo-2,3,4-trifluorobenzoic acid

생성물 1

HCID 218669915-Bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid수율 66.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of LiHMDS (49.0 mL, 2 M in THF/heptane) in THF (40 mL) was added 2-chlorophenylamine (6.50 mL, 60.6 mmol) at −78° C. After vigorous stirring for 10 minutes, a solution of 5-bromo-2,3,4-trifluoro-benzoic acid (2) (7.70 g, 30.2 mmol) in THF (60 mL) was added. The dry-ice bath was removed and the reaction mixture stirred for 4 hours at room temperature. The mixture was concentrated, treated with 10% aqueous HCl (75 mL), and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered, and concentrated. Purification by trituration with boiling CH2Cl2 gave 7.24 g (66%) of the desired acid (3) as a yellow solid

후처리

  1. customThe dry-ice bath was removed
  2. stirringthe reaction mixture stirred for 4 hours at room temperature
  3. concentrationThe mixture was concentrated
  4. additiontreated with 10% aqueous HCl (75 mL)
  5. extractionextracted with EtOAc
  6. dry with materialThe combined organic extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by trituration with boiling CH2Cl2

출처 및 근거

ORD 기록
ord-d35fb952c63e4d738d1ca0bf9a1c78c9
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538120B2

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