Carbon tetrabromide → [(Z)-3-bromoprop-1-enyl]-tributylstannane

HRID 927904Notes

Reaction equation

HRID 927904 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([Sn:24]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:29][CH2:30][CH2:31][CH3:32])/[CH:25]=[CH:26]\[CH2:27]O)[CH2:21][CH2:22][CH3:23].C(Br)(Br)(Br)[Br:38]>C(Cl)Cl>[Br:38][CH2:27]/[CH:26]=[CH:25]\[Sn:24]([CH2:33][CH2:34][CH2:35][CH3:36])([CH2:29][CH2:30][CH2:31][CH3:32])[CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 9974944(Z)-3-(Tributylstannyl)prop-2-en-1-ol2×

Product 1

HCID 10949620[(Z)-3-bromoprop-1-enyl]-tributylstannaneYield 160.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of triphenylphosphine (5.32 g) in DCM (60 mL) was added to a solution of (Z)-3-tributylstannanylprop-2-en-1-ol (Intermediate 13, 6.4 g) and carbon tetrabromide (9.18 g) in DCM (60 mL) and the mixture was stirred for 2.5 hours. The mixture was evaporated to low volume and pentane was added. The solids were removed by filtration and the filtrate was evaporated to dryness. Pentane was added and the solids were again removed by filtration and the filtrate was evaporated to dryness to give ((Z)-3-bromoprop-1-enyl)-tributylstannane (12.14 g) as an oil.

Workup

  1. customThe mixture was evaporated to low volume and pentane
  2. additionwas added
  3. customThe solids were removed by filtration
  4. customthe filtrate was evaporated to dryness
  5. additionPentane was added
  6. customthe solids were again removed by filtration
  7. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-d098e8661b47401ca6740fb2163008d6
Source dataset
uspto-grants-2016_03
Patent number
US09290472B2

Reaction notes

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