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

HRID 1157923

反応式

HRID 1157923 の反応式
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

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 707414-BromobenzaldehydeHCID 27339602-Thiopheneboronic acid

生成物 1

HCID 7364994-(Thiophen-2-yl)benzaldehyde収率 78%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 22732251Tetrahydrofuran dimethoxyethane溶媒

反応条件

温度
85 °C

実験手順

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) δ 7.14 (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).

後処理

  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)

出典と根拠

ORDレコード
ord-f46b556e1f2c443693c6a5652c3b622f
出典データセット
uspto-grants-2010_10
特許番号
US07807694B2

関連ノート

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