Carbon tetrabromide → HCID 21866480, compound

HRID 1582919Notes

Reaction equation

HRID 1582919 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][C:22]1[S:26][C:25]([C:27]#[N:28])=[C:24]([CH3:29])[CH:23]=1.[Br:30]C(Br)(Br)Br>O1CCCC1>[Br:30][CH2:21][C:22]1[S:26][C:25]([C:27]#[N:28])=[C:24]([CH3:29])[CH:23]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21866516HCID 21866516, compound

Product 1

HCID 21866480HCID 21866480, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

44 g (167 mmol) of triphenylphosphine were added to a solution of 24 g (152 mmol) of 5-hydroxymethyl-3-methylthiophene-2-carbonitrile in 180 ml of tetrahydrofuran. Then, a solution of 55 g (167 mmol) of tetrabromomethane in 100 ml of tetrahydrofuran was added. The mixture was stirred for 90 minutes 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 hexane:ethyl acetate 8:2). This gave 34 g of the title compound which still contained a small amount of solvent. 1H NMR (270 MHz, DMSO-d6): δ=2.4 (s, 3H), 5.0 (s, 2H), 7.3 (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 hexane:ethyl acetate 8:2)

Sources & evidence

ORD record
ord-7465d5a1e824401783d4718bc90673df
Source dataset
uspto-grants-2004_05
Patent number
US06740647B1

Reaction notes

Loading…