Ammonium Chloride → Methyl 2-amino-5-phenylbenzoate

HRID 1070392노트

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HRID 1070392 반응식
[NH2:1][C:2]1[CH:11]=[CH:10][C:9](Br)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>O1CCOCC1.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>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 736224Methyl 2-amino-5-bromobenzoate

생성물 1

HCID 16768797Methyl 2-amino-5-phenylbenzoate수율 73.3%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

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온도
85 °C

실험 절차

To a solution of methyl 2-amino-5-bromobenzoate (2.0 g, 8.7 mmol) in dioxane (40 mL) were added phenylboronic acid (1.91 g, 15.7 mmol), potassium phosphate (4.08 g, 19.1 mmol) and tetrakis(triphenylphosphine)palladium (0.26 g, 0.22 mmol) under nitrogen. The mixture was heated at 85° C. for 20 h, then cooled to 0-5° C. Aqueous ammonium chloride was added and the mixture was extracted, washed with brine, dried (Na2SO4) and concentrated to dryness. Purification by chromatography gave 1.45 g of methyl 2-amino-5-phenylbenzoate.

후처리

  1. temperaturecooled to 0-5° C
  2. extractionthe mixture was extracted
  3. washwashed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to dryness
  6. customPurification by chromatography

출처 및 근거

ORD 기록
ord-413eecf01edc47db99f6d12b91ff891e
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06903086B2

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