Water → 4'-(Benzyloxy)-4-fluoro-2',6'-dimethylbiphenyl-3-carbaldehyde

HRID 2280669노트

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HRID 2280669 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12](B(O)O)=[C:11]([CH3:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:20][C:21]1[CH:28]=[CH:27][C:26](Br)=[CH:25][C:22]=1[CH:23]=[O:24].C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:26]2[CH:27]=[CH:28][C:21]([F:20])=[C:22]([CH:23]=[O:24])[CH:25]=2)=[C:11]([CH3:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

9

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 23157199(4-(Benzyloxy)-2,6-dimethylphenyl)boronic acid

생성물 1

HCID 897017664'-(Benzyloxy)-4-fluoro-2',6'-dimethylbiphenyl-3-carbaldehyde수율 116.6%

시약·촉매·용매 4

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매HCID 1140Toluene용매HCID 80711,2-Dimethoxyethane용매

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온도
100 °C

실험 절차

(4-(Benzyloxy)-2,6-dimethylphenyl)boronic acid 12b (256 mg, 1 mmol), 2-fluoro-5-bromo-benzaldehyde (203 mg, 1 mmol), 2M aqueous sodium carbonate solution (1 mL, 2 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (37 mg, 0.08 mmol) and tris(dibenzylideneacetone)dipalladium (18 mg, 0.02 mmol) were dissolved in 3 mL of a mixture of the solvents ethylene glycol dimethyl ether and toluene (V/V=1:2). The reaction mixture was heated at 100° C. for 2 hours, and then at 120° C. for 0.5 hours under microwave conditions. The resulting mixture was mixed with 10 mL of water and extracted with ethyl acetate (10 mL×3). The combined organic extracts were washed with saturated sodium chloride solution (30 mL), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with elution system B to obtain the title compound 4′-(benzyloxy)-4-fluoro-2′,6′-dimethylbiphenyl-3-carbaldehyde 18a (390 mg, yield 58.4%) as a colorless slime.

후처리

  1. extractionextracted with ethyl acetate (10 mL×3)
  2. washThe combined organic extracts were washed with saturated sodium chloride solution (30 mL)
  3. dry with materialdried with anhydrous magnesium sulphate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography with elution system B

출처 및 근거

ORD 기록
ord-4a878c20b66b4bb5ae5a86355ec40e88
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09139548B2

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