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Sodium Carbonate → 4-(2-Acetylphenyl)benzoic acid

HRID 2244247
ノート
印刷プレビュー

反応式

HRID 2244247 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([OH:3])=[O:2].Br[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20](=[O:22])[CH3:21].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.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:20]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:7]1[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=1)(=[O:22])[CH3:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 750602'-BromoacetophenoneHCID 3121834-Carboxyphenylboronic Acid

生成物 1

HCID 200999564-(2-Acetylphenyl)benzoic acid収率 91%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒
HCID 6342
Acetonitrile
溶媒

反応条件

温度
90 °C

実験手順

To a suspension of 4-carboxybenzeneboronic acid (2.0 g, 12.1 mmol) and 1-(2-bromo-phenyl)-ethanone (1.63 mL, 12.1 mmol) in dry acetonitrile (60 mL) was added a 0.4 M aqueous sodium carbonate solution (60 mL) and the reaction mixture purged with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.5 g, 0.433 mmol) was then added and the reaction mixture heated to 90° C. for 22 hours. The hot reaction mixture was filtered through celite and then concentrated in vacuo to remove acetonitrile. The resulting aqueous suspension was diluted with water to 75 mL then washed with diethyl ether (75 mL). The aqueous phase was acidified to pH 1 by the addition of concentrated hydrochloric acid and the resulting white suspension cooled to 4° C. for 1 hour. The solid product was filtered, washed with water and then dried in vacuo at 50° C. overnight to afford the title compound (2.62 g, 91%) as a white solid, m.p. 199-201° C.

後処理

  1. customthe reaction mixture purged with nitrogen for 10 minutes
  2. filtrationThe hot reaction mixture was filtered through celite
  3. concentrationconcentrated in vacuo
  4. customto remove acetonitrile
  5. additionThe resulting aqueous suspension was diluted with water to 75 mL
  6. washthen washed with diethyl ether (75 mL)
  7. additionThe aqueous phase was acidified to pH 1 by the addition of concentrated hydrochloric acid
  8. temperaturethe resulting white suspension cooled to 4° C. for 1 hour
  9. filtrationThe solid product was filtered
  10. washwashed with water
  11. customdried in vacuo at 50° C. overnight

出典と根拠

ORDレコード
ord-3b4215882d5c4d8eb75d58dff4a2f144
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07678787B2

反応ノート

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