2-Bromophenol → 2-(1-Methyl-1H-pyrrol-2-yl)phenol

HRID 1908036노트

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HRID 1908036 반응식
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1B1OC(C)(C)C(C)(C)O1.Br[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23].C(=O)([O-])[O-].[K+].[K+]>ClCCCl.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>[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23]

참가 물질

6

반응물 3

HCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 441187731-Methyl-1H-pyrrole-2-boronic acid, pinacol ester

생성물 1

HCID 220904482-(1-Methyl-1H-pyrrol-2-yl)phenol수율 34%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 111,2-Dichloroethane용매

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온도
80 °C

실험 절차

1-Methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrole (5.0 g, 24 mmol), tetrakis(triphenylphosphine)palladium (0) (1.4 g, 1.2 mmol), 2-bromophenol (4.2 g, 24 mmol), and potassium carbonate (24 mL of 2.0 M, 48 mmol) were combined in 1,2-dichloroethane (291 mL). The mixture was heated at 80° C. for 16 h. The mixture was cooled to 25° C. before it was partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed with brine, dried over Na2SO4, and concentrated. Column chromatography (0-100% ethyl acetate/hexanes) on the residue gave 2-(1-methylpyrrol-2-yl)phenol (1.4 g, 34%). ESI-MS m/z calc. 173.2. found 174.2 (M+1)+; Retention time: 1.76 minutes (3 min run).

후처리

  1. temperatureThe mixture was cooled to 25° C. before it
  2. customwas partitioned between ethyl acetate and water
  3. customThe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4c2fd34349a846c4b400efe2916c475d
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08598164B2

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