Imidazole → [2-Bromo-1-(bromomethyl)ethoxy](tert-butyl)diphenylsilane

HRID 1426279Notes

Reaction equation

HRID 1426279 reaction equation
[Br:1][CH2:2][CH:3]([OH:6])[CH2:4][Br:5].N1C=CN=C1.[C:12]([Si:16](Cl)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:15])([CH3:14])[CH3:13]>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)C>[Br:1][CH2:2][CH:3]([CH2:4][Br:5])[O:6][Si:16]([C:12]([CH3:15])([CH3:14])[CH3:13])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 3

HCID 795ImidazoleHCID 72871,3-Dibromo-2-propanolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 69673452[2-Bromo-1-(bromomethyl)ethoxy](tert-butyl)diphenylsilaneYield 100.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,3-dibromo-2-propanol (20.00 g, 91.79 mmol) in methylene chloride (DCM) (100 mL) cooled to 0° C. was added 1H-imidazole (6.56 g, 96.4 mmol) followed by tert-butylchlorodiphenylsilane (25.1 mL, 96.4 mmol) and 4-dimethylaminopyridine (1.12 g, 9.18 mmol). The reaction was stirred with warming to room temperature overnight. The reaction mixture was diluted with diethyl ether, washed with water, and the aqueous layer was again extracted once with ether. The combined organic extracts were washed with water, followed by brine, dried over sodium sulfate, decanted and concentrated. Flash chromatography (eluting with a gradient from 0-15% ethyl acetate/hexanes) afforded desired product (42 g, 100%). 1H NMR (300 MHz, CDCl3): δ 7.72-7.66 (m, 4H), 7.51-7.37 (m, 6H), 4.00-3.91 (m, 1H), 3.49-3.45 (m, 4H), 1.09 (s, 9H).

Workup

  1. washwashed with water
  2. extractionthe aqueous layer was again extracted once with ether
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried over sodium sulfate
  5. customdecanted
  6. concentrationconcentrated
  7. washFlash chromatography (eluting with a gradient from 0-15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-506962138b014f90bef13193e9f54dc1
Source dataset
uspto-grants-2015_01
Patent number
US08933085B2

Reaction notes

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