Imidazole → (4-(2-Bromoethyl)phenoxy)(tert-butyl)dimethylsilane

HRID 1878759

反応式

HRID 1878759 の反応式
[Si:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16]O)=[CH:11][CH:10]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[Br:42]Br>C(#N)C.C(OCC)C>[Br:42][CH2:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:10][CH:11]=1

参加物

7

反応物 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 112882212-(4-((Tert-butyldimethylsilyl)oxy)phenyl)ethan-1-ol

生成物 1

HCID 636962(4-(2-Bromoethyl)phenoxy)(tert-butyl)dimethylsilane

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
23 °C

実験手順

To a stirring solution of 2-(4-(tert-butyldimethylsilyloxy)phenyl)ethanol (1250 mg, 4.95 mmol) in acetonitrile (50 mL) and diethyl ether (25 mL) was sequentially added triphenylphosphine (3.44 mL, 14.8 mmol), 1H-imidazole (1011 mg, 14.8 μmol), and bromine (765 μl, 14.8 mmol). The clear solution was stirred at 23° C. for 18 h. The mixture was concentrated directly onto silica (20 g) under reduced pressure then purified on 120 grams of silica eluting with 0-5% EtOAc/Hexane. MS (ESI pos. ion) m/z (MH+): 315/317. Calc'd exact mass for C14H23BrOSi: 314. 1H NMR (400 MHz, Chloroform-d) δ ppm 0.19 (s, 6 H) 0.98 (s, 9 H) 3.08 (t, J=7.78 Hz, 2 H) 3.47-3.57 (m, 2 H) 6.78 (d, J=8.53 Hz, 2 H) 7.05 (d, J=8.53 Hz, 2 H).

後処理

  1. concentrationThe mixture was concentrated directly onto silica (20 g) under reduced pressure
  2. customthen purified on 120 grams of silica eluting with 0-5% EtOAc/Hexane

出典と根拠

ORDレコード
ord-6f4ea63b5fe84b42b80b138c1e81a2a8
出典データセット
uspto-grants-2012_11
特許番号
US08314087B2

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