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

HRID 1499122노트

반응식

HRID 1499122 반응식
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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 22287110N-methylpyrrolidone-water용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-20381d8e3b20480f9535fbeed6a5cd8c
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09199994B2

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