Diethyl Ether → 5-Phenylthiophene-2-carbaldehyde

HRID 412004

반응식

HRID 412004 반응식
Br[C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])([O-])=O.[Na+].[Na+].CCOCC>C1COCC1.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>[C:9]1([C:2]2[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

참가 물질

7

반응물 4

HCID 3283Diethyl EtherHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 784285-Bromothiophene-2-carbaldehyde

생성물 1

HCID 1770535-Phenylthiophene-2-carbaldehyde수율 91.9%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

5-Bromothiophene-2-carboxaldehyde (1.0 g, 5.2 mmol) is added to a solution of tetrakis(triphenylphosphine)palladium(0) (180 mg, 0.16 mol) in degassed THF (10 mL). The resulting solution is stirred for 5 minutes and then a solution of phenylboronic acid (760 mg, 6.2 mmol) in THF (10 mL) is added followed by aqueous Na2CO3 (2M, 5.2 mL). The mixture is heated at reflux for 24 h. The reaction mixture is allowed to cool, poured into ether, and washed twice with water. The ether layer is dried over Na2SO4 and concentrated in vacuo. The crude product is purified by flash column chromatography (1:1 hexanes/CH2Cl2) to yield 900 mg (91%) of 5-phenylthiophene-2-carboxaldehyde. 1H NMR (300MHz, CDCl3)δ7.38-7.45, 7.65-7.68, 7.73, 9.88.

후처리

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 24 h
  3. temperatureto cool
  4. washwashed twice with water
  5. dry with materialThe ether layer is dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by flash column chromatography (1:1 hexanes/CH2Cl2)

출처 및 근거

ORD 기록
ord-9042e8cf7efe4b88ac999d58addddc10
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562816B2

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