Bromobenzene → 4-Bromo-2,6-dimethylbiphenyl

HRID 252245ノート

反応式

HRID 252245 の反応式
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Br:13][C:14]1[CH:15]=[C:16]([CH3:22])[C:17](I)=[C:18]([CH3:20])[CH:19]=1>O1CCCC1.[Cl-].[Zn+2].[Cl-]>[Br:13][C:14]1[CH:15]=[C:16]([CH3:22])[C:17]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:18]([CH3:20])[CH:19]=1

参加物

6

反応物 3

HCID 7961BromobenzeneHCID 27355735-Bromo-2-iodo-1,3-dimethylbenzeneHCID 178418339Butyllithium

生成物 1

HCID 668578334-Bromo-2,6-dimethylbiphenyl収率 33%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

2.5 M n-Butyllithium, in tetrahydrofuran, (1.42 ml, 3.54 mmol, 1.1 equiv.) was added dropwise to a solution of bromobenzene (0.34 ml, 3.22 mmol, 1.0 equiv.) in dry tetrahydrofuran (18 ml), under nitrogen at −78° C. and the mixture stirred for 30 minutes. Zinc chloride (0.48 g, 3.54 mmol, 1.1 equiv.) was added and the mixture allowed to warm to room temperature while stirring for 2 hours. Palladium tetrakistriphenylphosphine (0.19 g, 0.16 mmol, 0.05 equiv.) and a solution of 5-bromo-2-iodo-1,3-dimethyl-benzene (1.00 g, 3.22 mmol, 1.0 equiv.) in tetrahydrofuran (2 ml) were added and the mixture stirred at room temperature for 16 hours. The tetrahydrofuran was evaporated under reduced pressure and the crude product purified by column chromatography (SiO2, heptane). The fractions were combined to afford 4-bromo-2,6-dimethylbiphenyl, 278 mg (33% yield) as a clear oil δH (400 MHz; d4-methanol) 7.28-7.39 (3H, m), 7.18 (2H, s), 7.03 (2H, d), 1.90 (6H, s).

後処理

  1. stirringwhile stirring for 2 hours
  2. stirringthe mixture stirred at room temperature for 16 hours
  3. customThe tetrahydrofuran was evaporated under reduced pressure
  4. customthe crude product purified by column chromatography (SiO2, heptane)

出典と根拠

ORDレコード
ord-64351bf6b77c47379671e216238805c3
出典データセット
uspto-grants-2011_01
特許番号
US07868030B2

反応ノート

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