4-Bromotoluene → 4-Methylbiphenyl

HRID 13872

반응식

HRID 13872 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[C:9]1([Mg]Cl)[CH:14]=[CH:13]C=[CH:11][CH:10]=1.[Cl-].[NH4+].O1CCC[CH2:20]1>[Pd](Cl)Cl.C(N(CC)CC)C.C1([B-](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C>[CH3:20][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=2)=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 78054-BromotolueneHCID 8028Tetrahydrofuran2회HCID 25517Ammonium ChlorideHCID 178478979HCID 178478979, 화합물

생성물 1

HCID 125664-Methylbiphenyl

시약·촉매·용매 3

HCID 8471Triethylamine촉매HCID 24290Palladium Chloride촉매HCID 23136663Tri-tert-butylphosphonium Tetraphenylborate촉매

실험 절차

A 30-ml four-necked flask was equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser. 0.014 g (0.08 mmol) of palladium (II) chloride, 0.0194 g (0.19 mmol) of triethylamine and 5.5 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.084 g (0.16 mmol) of tri-tert-butylphosphonium tetraphenylborate obtained in Example A-1 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 21° C. for 30 minutes. 1.368 g (8 mmol) of 4-bromotoluene was added, followed by stirring at 21° C. for 30 minutes. 4 ml (8.8 mmol) of 2.2M tetrahydrofuran solution of phenylmagnesium chloride was added dropwise at 21° C. over a period of 10 minutes, followed by stirring at 21° C. for 2 hours. After the completion of the reaction, 5 ml of saturated aqueous ammonium chloride solution was added, followed by separation. The organic phase was purified by column chromatography to afford 1.175 g of 4-methylbiphenyl (yield: 87 mol % based on 4-bromotoluene). The identification of the product was made by mass spectroscopy.

후처리

  1. customA 30-ml four-necked flask was equipped with a stirrer
  2. additionadded into the flask
  3. customThe flask was purged with argon
  4. stirringby stirring at 21° C. for 30 minutes
  5. stirringby stirring at 21° C. for 30 minutes
  6. stirringby stirring at 21° C. for 2 hours
  7. additionwas added
  8. customfollowed by separation
  9. customThe organic phase was purified by column chromatography

출처 및 근거

ORD 기록
ord-a35008c257ca44deabe8bd94b2645a87
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728176B2

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