Hydrochloric Acid → Methyl (3'-benzyloxy-4'-methoxybiphenyl-3-yl)acetate

HRID 2247437

반응식

HRID 2247437 반응식
[CH2:1]([O:8][CH:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1([O:18][CH3:19])B(O)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C(O)C.C(=O)([O-])[O-].[K+].[K+].Br[C:32]1[CH:33]=[C:34]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[CH:35]=[CH:36][CH:37]=1.Cl>C(OCC)C.COCCOC.[Pd].ClC1[C-](P)C(C2C=CC=CC=2)=C(C2C=CC=CC=2)C=1Cl.[CH-]1C=CC=C1.[Fe+2]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:36]2[CH:37]=[CH:32][CH:33]=[C:34]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[CH:35]=2)[CH:12]=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 1030Propylene GlycolHCID 11430Potassium CarbonateHCID 11746402Methyl 2-(3-bromophenyl)acetateHCID 686332012-Benzyloxy-1-methoxybenzeneboronic acid

생성물 1

HCID 59219255Methyl (3'-benzyloxy-4'-methoxybiphenyl-3-yl)acetate수율 55.5%

시약·촉매·용매 3

HCID 178527692HCID 178527692, 화합물촉매HCID 3283Diethyl Ether용매HCID 80711,2-Dimethoxyethane용매

실험 절차

1.753 g of 2-Benzyloxy-1-methoxybenzeneboronic acid was suspended in 50 ml of diethyl ether, and 0.49 ml of propylene glycol was added thereto. The mixture was stirred at room temperature for 1 hour, and the solvent was removed to give 2-(3-benzyloxy-4-methoxyphenyl)-[1,3,2]dioxaborynane. This product was dissolved in 30 ml of 1,2-dimethoxyethane, then 1.5 g of potassium carbonate, 1.9 g of methyl 3-bromophenylacetate and 270 mg of dichlorodiphenyl phosphinoferrocene palladium were added thereto, and the mixture was stirred at 80° C. for 3 hours in a nitrogen atmosphere. The reaction mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography, to give 1.356 g of the title compound in the 6:1→4:1 fraction.

후처리

  1. customthe solvent was removed
  2. customto give 2-(3-benzyloxy-4-methoxyphenyl)-[1,3,2]dioxaborynane
  3. stirringthe mixture was stirred at 80° C. for 3 hours in a nitrogen atmosphere
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-1e524e2bacc5478e973d7ae9fb5b2da0
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07687664B2

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