Sodium Carbonate → 4-(Thiophen-2-yl)benzaldehyde

HRID 1582315

반응식

HRID 1582315 반응식
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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>[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 707414-BromobenzaldehydeHCID 27339602-Thiopheneboronic acid

생성물 1

HCID 7364994-(Thiophen-2-yl)benzaldehyde수율 78%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 22732251Tetrahydrofuran dimethoxyethane용매

반응 조건

온도
85 °C

실험 절차

To a stirred degassed solution of 4-bromobenzaldehyde (371 mg, 2.00 mmol) and thiophene-2-boronic acid (287 mg, 2.24 mmol) in DME/THF (5 mL, 4:1) were added a 2 M Na2CO3 solution (3.0 mL) and Pd(PPh3)4 (110 mg, 0.095 mmol). The reaction mixture was flushed with argon and maintained under argon while being heated at 85° C. over 2 days. The mixture was then cooled and diluted with EtOAc (35 mL) and water (30 mL). The aqueous layer was washed with EtOAc (2×10 mL) and the combined organic extracts dried (Na2SO4), filtered and concentrated. Purification of the resultant oil by column chromatography on silica gel (Hexanes/EtOAc, 4:1) afforded the title compound (293 mg, 78%) as a yellow solid. 1H NMR (CDCl3) δ7.14 (dd, 1H, J=5.1, 3.6 Hz), 7.40 (dd, 1H, J=5.1, 0.9 Hz), 7.46 (dd, 1H, J=3.6, 0.9 Hz), 7.76 (d, 2H, J=8.4 Hz), 7.88 (d, 2H, J=8.4 Hz), 10.00 (s, 1H).

후처리

  1. customThe reaction mixture was flushed with argon
  2. temperaturemaintained under argon
  3. temperatureThe mixture was then cooled
  4. additiondiluted with EtOAc (35 mL) and water (30 mL)
  5. washThe aqueous layer was washed with EtOAc (2×10 mL)
  6. dry with materialthe combined organic extracts dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the resultant oil by column chromatography on silica gel (Hexanes/EtOAc, 4:1)

출처 및 근거

ORD 기록
ord-698c8ef9886d4a3199322a82073ee36a
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734191B2

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