Carbon tetrabromide → (5-Bromo-pent-2-ynyloxy)-tert-butyl-diphenyl-silane

HRID 1514336Notes

Reaction equation

HRID 1514336 reaction equation
[C:1]([Si:5]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[O:6][CH2:7][C:8]#[C:9][CH2:10][CH2:11]O)([CH3:4])([CH3:3])[CH3:2].C(Br)(Br)(Br)[Br:26].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[Br:26][CH2:11][CH2:10][C:9]#[C:8][CH2:7][O:6][Si:5]([C:1]([CH3:2])([CH3:4])[CH3:3])([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 142175645-{[tert-Butyl(diphenyl)silyl]oxy}pent-3-yn-1-ol

Product 1

HCID 57829248(5-Bromo-pent-2-ynyloxy)-tert-butyl-diphenyl-silaneYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of compound 5 (1.09 g, 3.22 mmol) and CBr4 (1.28 g, 3.86 mmol) in CH2Cl2 (70 mL) was treated with a solution of Ph3P (1.27 g, 4.84 mmol) in CH2Cl2 (30 mL) dropwise at −78° C. After 30 min, the reaction mixture was slowly warmed up to room temperature for 2 h and then stirred for overnight. The reaction mixture was poured to the silica gel pad. The filtrate was concentrated to dryness. After concentration, the residue was purified with 0˜2% EtOAc in hexanes by silica gel column chromatography to give 1.28 g of product 6 (3.19 mmol, 99% yield); 1H NMR (CDCl3) δ 7.80˜7.65 (m, 4H), 7.50˜7.32 (m, 6H), 4.34 (t, J=1.9 Hz, 1H), 3.35 (t, J=5.8 Hz, 2H), 2.73 (tt, J=2.1, 6.0 Hz, 2H) 1.08 (s, 9H).

Workup

  1. additionThe reaction mixture was poured to the silica gel pad
  2. concentrationThe filtrate was concentrated to dryness
  3. concentrationAfter concentration
  4. customthe residue was purified with 0˜2% EtOAc in hexanes by silica gel column chromatography

Sources & evidence

ORD record
ord-2ce2e4a623b5420e8944b82b9d21219c
Source dataset
uspto-grants-2012_07
Patent number
US08222257B2

Reaction notes

Loading…