Diethyl Ether → 2,6-Bis(methoxymethoxy)biphenyl

HRID 1511227노트

반응식

HRID 1511227 반응식
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].I[C:19]1[C:24]([O:25][CH2:26][O:27][CH3:28])=[CH:23][CH:22]=[CH:21][C:20]=1[O:29][CH2:30][O:31][CH3:32].CCOCC>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH3:32][O:31][CH2:30][O:29][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([O:25][CH2:26][O:27][CH3:28])[C:19]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

8

반응물 4

HCID 3283Diethyl EtherHCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 251387872-Iodo-1,3-bis(methoxymethoxy)benzene

생성물 1

HCID 251401012,6-Bis(methoxymethoxy)biphenyl수율 99%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl촉매HCID 1140Toluene용매2회

실험 절차

Anhydrous toluene (2.0 mL) was added to a flask charged with Pd2(dba)3 (56.3 mg, 0.062 mmol), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (50.5 mg, 0.12 mmol), phenylboronic acid (281 mg, 2.31 mmol), and potassium phosphate (979 mg, 4.61 mmol) at room temperature. After 15 minutes, a solution of 15 (500 mg, 1.54 mmol) in anhydrous toluene (1.0 mL) was added and the resulting solution was heated to reflux for 12 hours. Upon cooling to room temperature, ether was added, the solution was filtered through SiO2 and concentrated to give 16 as a colorless amorphous solid (418 mg, 99%): 1H NMR (CDCl3, 500 MHz) 7.35-7.28 (m, 2H), 7.28-7.25 (m, 2H), 7.18-7.15 (m, 2H), 6.83 (d, J=8.3 Hz, 2H), 4.96 (s, 4H), 3.24 (s, 6H); 13C NMR (CDCl3, 125 MHz) 155.3, 155.0, 134.3, 130.8, 129.5, 128.7, 128.0, 127.6, 126.8, 122.6, 109.4 (2C), 94.9 (2C), 56.0 (2C); IR (film) νmax 2955, 2928, 2901, 2359, 2341, 1587, 1466, 1439, 1400, 1244, 1153, 1099, 1080, 1041, 922, 764, 733, 700 cm−1; HRMS (ESI+) m/z: [M+Na]+ calcd for C16H18O4, 297.1103. found, 297.1052.

후처리

  1. temperaturethe resulting solution was heated
  2. temperatureto reflux for 12 hours
  3. filtrationthe solution was filtered through SiO2
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3664bbfadeaa45ea9038f179ed66dd90
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08212011B2

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