Sodium Carbonate → Methyl 3-benzylbenzoate

HRID 1777514노트

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HRID 1777514 반응식
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C(COC)OC.ClCCl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:2]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 517981Methyl 3-(bromomethyl)benzoate

생성물 1

HCID 597640Methyl 3-benzylbenzoate수율 84.2%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 6344Dichloromethane용매HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of methyl 3-(bromomethyl)benzoate (1.50 g; 6.35 mmol), phenylboronic acid (0.790 g; 6.35 mmol), sodium carbonate (1.35 g; 12.70 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.074 g; 0.063 mmol) in water (4 mL) and dimethoxyethane (12 mL) was irradiated in a microwave oven at 130° C. for 10 minutes. The mixture was diluted with dichloromethane and washed with a saturated aqueous solution of sodium bicarbonate. The organic layer was concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 15 to 100% dichloromethane in heptane) to afford 1.21 g (84%) of methyl 3-benzylbenzoate.

후처리

  1. customwas irradiated in a microwave oven at 130° C. for 10 minutes
  2. washwashed with a saturated aqueous solution of sodium bicarbonate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe crude material was purified by flash chromatography on silica gel (eluent 15 to 100% dichloromethane in heptane)

출처 및 근거

ORD 기록
ord-5376da9d210140ab9a525ae6618ed12b
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266832B2

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