Sodium Carbonate → 2'-Methoxy-[1,1'-biphenyl]-4-carbaldehyde

HRID 1582313

反応式

HRID 1582313 の反応式
Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=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>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=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 27339582-Methoxyphenylboronic acid

生成物 1

HCID 27595432'-Methoxy-[1,1'-biphenyl]-4-carbaldehyde収率 92%

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 (218 mg, 1.18 mmol) and 2-methoxybenzeneboronic acid (188 mg, 1.24 mmol) in DME/THF (5 mL, 4:1) were added a 2 M Na2CO3 solution (1.6 mL) and Pd(PPh3)4 (63 mg, 0.055 mmol). The reaction mixture was flushed with argon and maintained under argon while being heated at 85° C. overnight. The mixture was then cooled and diluted with EtOAc (25 mL) and water (25 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 with silica gel (Hexanes/Et2O, 80:20) afforded the title compound (230 mg, 92%) as a clear oil. 1H NMR (CDCl3) δ3.84 (s, 3H), 7.01-7.09 (m, 2H), 7.33-7.39 (m, 2H), 7.71 (d, 2H, J=6 Hz), 7.93 (d, 2H, J=6 Hz), 10.05 (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 (25 mL) and water (25 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 with silica gel (Hexanes/Et2O, 80:20)

出典と根拠

ORDレコード
ord-f61fcdbb72cc41e188bc921119817496
出典データセット
uspto-grants-2004_05
特許番号
US06734191B2

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