Ethyl Acetate → 2'-Chloro-[1,1'-biphenyl]-2-carbaldehyde

HRID 1394154

反応式

HRID 1394154 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Cl:8].[CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O)=[O:10].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C1(C)C=CC=CC=1.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>[CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Cl:8])=[O:10]

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 127541-Bromo-2-chlorobenzeneHCID 2921892-Formylphenylboronic acid

生成物 1

HCID 13923752'-Chloro-[1,1'-biphenyl]-2-carbaldehyde

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

To a solution of 2-bromochlorobenzene (0.12 mL, 1 mmol) and 2-formylbenzeneboronic acid (0.17 g, 1.1 mmol) in toluene (9 mL) were added 2M aq. sodium carbonate (1.2 mL) followed by (Ph3P)4Pd (0.34 g, 0.3 mmol). The resulting reaction mixture was refluxed for 3 h, cooled and diluted ethyl acetate. The organic phase was washed with water, saturated aq. sodium bicarbonate, brine and dried over sodium sulfate. The filtrate was concentrated in vacuo and the residue obtained was purified by chromatography (hexane:ethyl acetate; 4:1) to yield the title product.

後処理

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 3 h
  3. temperaturecooled
  4. washThe organic phase was washed with water, saturated aq. sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. concentrationThe filtrate was concentrated in vacuo
  7. customthe residue obtained
  8. customwas purified by chromatography (hexane:ethyl acetate; 4:1)

出典と根拠

ORDレコード
ord-c2a9002fd6a140cba829b5dc2899c98a
出典データセット
uspto-grants-2008_03
特許番号
US07348348B2

関連ノート

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