Hydrochloric Acid → 5-Bromo-[1,1'-biphenyl]-2-carboxylic acid

HRID 1499122ノート

反応式

HRID 1499122 の反応式
Br[C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Li+].[OH-].Cl>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].CN1C(=O)CCC1.O>[Br:11][C:9]1[CH:10]=[C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]([C:4]([OH:6])=[O:5])=[CH:7][CH:8]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 118962,4-Dibromobenzoic acidHCID 66827Phenylboronic Acid

生成物 1

HCID 234361085-Bromo-[1,1'-biphenyl]-2-carboxylic acid

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 22287110N-methylpyrrolidone-water溶媒

反応条件

温度
70 °C

実験手順

A solution of 2,4-dibromo-benzoic acid, (2.3 g, 18.8 mmol), phenyl boronic acid (5 g, 17.9 mmol), Pd2(dba)3 (818 mg, 8.9 mmol) and LiOH (1.65 g, 39.3 mmol) in a 1:1 mixture of NMP/water (100 mL) was heated to 70° C. for 2 d. After this time, the reaction mixture was cooled to RT, and the reaction mixture was adjusted to pH=4-5 with 3 N HCl. The mixture was then extracted with ethyl acetate and the combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo and purified by normal phase silica gel column (EtOAc/PE 10:1 to 1:1) to afford 5-bromo-[1,1′-biphenyl]-2-carboxylic acid as a colorless oil.

後処理

  1. temperatureAfter this time, the reaction mixture was cooled to RT
  2. extractionThe mixture was then extracted with ethyl acetate
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by normal phase silica gel column (EtOAc/PE 10:1 to 1:1)

出典と根拠

ORDレコード
ord-20381d8e3b20480f9535fbeed6a5cd8c
出典データセット
uspto-grants-2015_12
特許番号
US09199994B2

反応ノート

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