Carbon tetrabromide → (4-(2-Bromoethyl)-3,5-difluorophenoxy)triisopropylsilane

HRID 82788Notes

Reaction equation

HRID 82788 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:20]([Br:24])(Br)(Br)Br.[F:25][C:26]1[CH:31]=[C:30]([O:32][Si:33]([CH:40]([CH3:42])[CH3:41])([CH:37]([CH3:39])[CH3:38])[CH:34]([CH3:36])[CH3:35])[CH:29]=[C:28]([F:43])[C:27]=1[CH2:44]CO>C(Cl)Cl>[Br:24][CH2:20][CH2:44][C:27]1[C:26]([F:25])=[CH:31][C:30]([O:32][Si:33]([CH:40]([CH3:42])[CH3:41])([CH:34]([CH3:36])[CH3:35])[CH:37]([CH3:38])[CH3:39])=[CH:29][C:28]=1[F:43]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 682283852-(2,6-Difluoro-4-(triisopropylsilyloxy)phenyl)ethanol

Product 1

HCID 68004578(4-(2-Bromoethyl)-3,5-difluorophenoxy)triisopropylsilaneYield 67.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

PPh3 (1.11 g, 4.24 mmol) was added to a cooled (0° C.) solution of CBr4 (0.92 g, 237 mmol) in DCM (15 mL). After stirring for 15 minutes, a solution of PMW04155 (0.70 g, 2.12 mmol) in DCM (5 mL) was added and the reaction mixture was stirred for 1 h, then allowed to warm to room temperature and stirred for 2 h. The solvent was removed in vacuo and the residue was purified using the Combiflash system (EtOAc/PE) to give the title compound (0.56 g, 67%) as a colourless oil; 1H NMR (270 MHz, CDCl3) 1.05-1.32 (21H, m, 6×CH3,3×CH), 3.13 (2H, t, J=7.7, CH2), 3.48 (2H, t, J=7.7, CH2), 6.34-6.45 (2H, m, ArH).

Workup

  1. stirringthe reaction mixture was stirred for 1 h
  2. stirringstirred for 2 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified

Sources & evidence

ORD record
ord-4ce4c439488f4cbaa115d6f9b4dbd859
Source dataset
uspto-grants-2014_09
Patent number
US08846737B2

Reaction notes

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