Carbon tetrabromide → HCID 21866484, compound

HRID 1582923Notes

Reaction equation

HRID 1582923 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][C:22]1[S:26][CH:25]=[C:24]([C:27]#[N:28])[C:23]=1[CH3:29].[Br:30]C(Br)(Br)Br>O1CCCC1>[Br:30][CH2:21][C:22]1[S:26][CH:25]=[C:24]([C:27]#[N:28])[C:23]=1[CH3:29]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21866519HCID 21866519, compound

Product 1

HCID 21866484HCID 21866484, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

30 g (115 mmol) of triphenylphosphine were added at 5° C. to a solution of 16 g (104 mmol) of 5-hydroxymethyl-4-methylthiophene-3-carbonitrile in 300 ml of tetrahydrofuran. Then, a solution of 38 g (115 mmol) of tetrabromomethane in 100 ml of tetrahydrofuran was added. The mixture was stirred overnight at room temperature. The reaction mixture was concentrated on a rotary evaporator under a water pump vacuum and the residue was purified by column chromatography (eluant petroleum ether:dichloromethane 1:1). This gave 17 g (76%) of the title compound as yellow oil. 1H NMR (270 MHz, DMSO-d6): δ=2.25 (s, 3H), 5.0 (s, 2H), 8.5 (s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated on a rotary evaporator under a water pump vacuum
  2. customthe residue was purified by column chromatography (eluant petroleum ether:dichloromethane 1:1)

Sources & evidence

ORD record
ord-360b256d22284a95b3a4b302f46c8cd7
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

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