Hydrochloric Acid → F 1893

HRID 2053686

反応式

HRID 2053686 の反応式
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+].Cl>C1COCC1>[Cl:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:8]1[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1393555Methyl 2'-chloro-1,1'-biphenyl-4-carboxylate

生成物 1

HCID 160722F 1893収率 67%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Combine methyl-4-bromobenzoate (1.0 g, 4.65 mmol), 2-chlorophenylboronic acid (799 mg, 5.1 mmol), Pd(OAc)2 (51 mg, 0.46 mmol) and sodium carbonate (1.5 g, 13.9 mmol) in DMF (20 mL) and water (2.0 mL) with stirring. Purge the reaction mixture with argon, add triphenylphosphine (61 mg, 0.23 mmol) and purge again with argon. Place the sealed reaction in an oil bath maintained at 80° C. and allow to stir for 1 hour. Cool the reaction to room temperature, dilute with ethyl acetate and filter through a short plug of celite with additional ethyl acetate. Wash the organics with water, dry over MgSO4, filter and evaporate. Purification by flash column chromatography yields 2′-chlorobiphenyl-4-carboxylic acid methyl ester as a yellow solid. Dissolve the purified ester in THF (0.25M) and add an equal volume of 1M NaOH. Stir vigorously at room temperature for 15 hours. Upon completion, acidify the reaction with conc. HCl and extract with ethyl acetate. Evaporation of the solvent yields 762 mg (67%) of the title compound. MS (m/e): 231.1 (M−).

後処理

  1. extractionextract with ethyl acetate
  2. customEvaporation of the solvent

出典と根拠

ORDレコード
ord-1fef3cad33d04263a8a4170fa5a63e5d
出典データセット
uspto-grants-2008_02
特許番号
US07326731B2

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