Carbon tetrabromide → 5-(Bromomethyl)furan-2-carbonitrile

HRID 619866Notes

Reaction equation

HRID 619866 reaction equation
O[CH2:2][C:3]1[O:7][C:6]([C:8]#[N:9])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:30]>C1COCC1>[Br:30][CH2:2][C:3]1[O:7][C:6]([C:8]#[N:9])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 30214065-(Hydroxymethyl)furan-2-carbonitrile

Product 1

HCID 108213955-(Bromomethyl)furan-2-carbonitrileYield 85.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Hydoxymethylfuran-2-carbononitrile (1.12 g, 9.1 mmol) is dissolved in THF (75 mL), treated with triphenylphosphine (2.9 g, 11.06 mmol), carbon tetrabromide (3.78 g, 11.4 mmol) and stirred at room temperature for 18 hours. Standard workup yields the title compound (1.45 g, 7.8 mmol).

Sources & evidence

ORD record
ord-1cc42026e8f94da08317e6191a13eb07
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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