Carbon tetrabromide → 2-(Bromomethyl)-5-nitrothiophene

HRID 363510Notes

Reaction equation

HRID 363510 reaction equation
O[CH2:2][C:3]1[S:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:31]>ClCCl.[Cl-].[Na+].O>[Br:31][CH2:2][C:3]1[S:4][C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 332588(5-nitrothiophen-2-yl)methanol

Product 1

HCID 536851562-(Bromomethyl)-5-nitrothiopheneYield 72.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of 2-hydroxymethyl-5-nitro-thiophene (18.8 g, 118 mmol) in dichloromethane (500 ml) at 0° C. was added triphenylphosphine (3 1.5 g, 120 mmol) followed by carbon tetrabromide (39 g, 118 mmol). The mixture was stirred for 2 hours, poured into half saturated brine and extracted with dichloromethane. The organic layer was dried over magnesium sulphate and the solvent removed at reduced pressure. The crude product was purified by silica gel chromatography using 15% ethyl acetate/hexane as the eluant to give 2-bromomethyl-5-nitrothiophene (19 g, 61%) as a brown oil.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic layer was dried over magnesium sulphate
  3. customthe solvent removed at reduced pressure
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3338c9d0cca2472dbb0af75964cf6133
Source dataset
uspto-grants-1999_02
Patent number
US05874472

Reaction notes

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