Potassium Carbonate → Tert-butyl 5-chloro-4-((2,2-dimethylchroman-7-yloxy)methyl)-2-fluorobenzoate

HRID 1849521노트

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HRID 1849521 반응식
[CH3:1][C:2]1([CH3:13])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([OH:12])=[CH:7][CH:8]=2)[O:3]1.Br[CH2:15][C:16]1[C:28]([Cl:29])=[CH:27][C:19]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[C:18]([F:30])[CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:29][C:28]1[C:16]([CH2:15][O:12][C:6]2[CH:5]=[C:4]3[C:9]([CH2:10][CH2:11][C:2]([CH3:13])([CH3:1])[O:3]3)=[CH:8][CH:7]=2)=[CH:17][C:18]([F:30])=[C:19]([CH:27]=1)[C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 110412812,2-dimethyl-3,4-dihydro-2H-1-benzopyran-7-olHCID 86702928HCID 86702928, 화합물

생성물 1

HCID 86702867Tert-butyl 5-chloro-4-((2,2-dimethylchroman-7-yloxy)methyl)-2-fluorobenzoate

시약·촉매·용매 1

HCID 180Acetone용매

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온도
50 °C

실험 절차

A mixture of 2,2-dimethylchroman-7-ol (100 mg, 0.561 mmol), tert-butyl 4-(bromomethyl)-5-chloro-2-fluorobenzoate (191 mg, 0.590 mmol) and potassium carbonate (194 mg, 1.40 mmol) in acetone (30 mL) was stirred at 50° C. for 16 hrs. After cooling to room temperature, the mixture was extracted with EtOAc (150×5 mL). The combined orgaic layers were washed with brine, dried over Na2SO4, filtered and concentrated to give the crude product which was used in next step without further purification (290 mg, crude). LCMS (ESI) m/z: 420.8 [M+H].

후처리

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with EtOAc (150×5 mL)
  3. washThe combined orgaic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-931b74e83ade41afb5978745ec36b14b
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952169B2

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