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

HRID 1908036ノート

反応式

HRID 1908036 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 111,2-Dichloroethane溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4c2fd34349a846c4b400efe2916c475d
出典データセット
uspto-grants-2013_12
特許番号
US08598164B2

反応ノート

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