5-Bromosalicylic acid → 4-Hydroxy[1,1'-biphenyl]-3-carboxylic acid

HRID 2086522

반응식

HRID 2086522 반응식
Br[C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=1.[C:12]1(OB(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].C(OC(=O)C)C.Cl>O>[C:12]1([C:2]2[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([OH:11])=[CH:4][CH:3]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 69725-Bromosalicylic acidHCID 11430Potassium CarbonateHCID 78412Phenyl dihydrogen orthoborateHCID 21866389Hydrogen chloride-ethyl acetate

생성물 1

HCID 675844-Hydroxy[1,1'-biphenyl]-3-carboxylic acid수율 89.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

In 400 ml of water, 21.7 g of 5-bromosalicylic acid, 13.41 g of phenylboric acid and 15.28 g of potassium carbonate were dissolved. The solution was stirred at room temperature for 40 minutes. After the completion of the reaction was confirmed with TLC, the reaction liquid was poured into a mixed medium of diluted hydrochloric acidethyl acetate. The mixture was extracted, and the organic phase was collected and washed with saturated sodium chloride aqueous solution. After dried with magnesium sulfate, the liquid was concentrated to form a crude product. The product was recrystallized from acetonitrile to obtain 18.58 g of 5-phenylsalicylic acid in the form of colorless crystallites. The yield was 87%. The product was confirmed with NMR and mass spectroscopy.

후처리

  1. customthe reaction liquid
  2. extractionThe mixture was extracted
  3. customthe organic phase was collected
  4. washwashed with saturated sodium chloride aqueous solution
  5. dry with materialAfter dried with magnesium sulfate
  6. concentrationthe liquid was concentrated
  7. customto form a crude product
  8. customThe product was recrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-e14dc147047b414ba7fc96fbc80376d9
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06726966B2

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