Bromobenzene → 4-Bromo-2,6-dimethylbiphenyl

HRID 252245

반응식

HRID 252245 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 668578334-Bromo-2,6-dimethylbiphenyl수율 33%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8028Tetrahydrofuran용매3회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-64351bf6b77c47379671e216238805c3
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868030B2

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