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

HRID 715943Notes

Reaction equation

HRID 715943 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 5, 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 concentrated 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. concentrationThe mixture was concentrated 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-5d4ea868d0cb41f6ace26503ab4224b3
Source dataset
uspto-grants-2015_11
Patent number
US09187494B2

Reaction notes

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