2-Bromonaphthalene → 4-(Naphthalen-2-yl)phenol

HRID 884719ノート

反応式

HRID 884719 の反応式
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[OH:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[CH:11][C:2]=1[C:16]1[CH:17]=[CH:18][C:13]([OH:12])=[CH:14][CH:15]=1

参加物

8

反応物 4

HCID 113722-BromonaphthaleneHCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 27343604-Hydroxyphenylboronic acid

生成物 1

HCID 2368684-(Naphthalen-2-yl)phenol収率 2.5%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a mixture of 2-bromonaphthalene (4.0 g, 19.32 mmol), 4-hydroxyphenylboronic acid (2.9 g, 21.24 mmol), potassium phosphate (14.35 g, 67.61 mmol), tricyclohexyl phosphine (542 mg, 1.93 mmol), toluene (80 mL) and water (4 mL) was added palladium acetate (217 mg, 0.965 mmol) under N2. The reaction mixture was heated to 100° C. for 24 h and then cooled to rt. Water was added and the mixture was extracted with EtOAc. The organic layer was separated, washed with water, brine, dried and concentrated to give crude product. Purification by column chromatography using 10% EtOAc in hexane afforded 105 mg of 4-naphthalen-2-yl-phenol. MS (ES) m/z: 220.07 (M) and 219.04 (M−1).

後処理

  1. temperaturecooled to rt
  2. extractionthe mixture was extracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. customdried
  6. concentrationconcentrated
  7. customto give crude product
  8. customPurification by column chromatography

出典と根拠

ORDレコード
ord-311807c4357149e9af4c762267da50a1
出典データセット
uspto-grants-2012_08
特許番号
US08242130B2

反応ノート

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