Carbon tetrabromide → 2-(Bromomethyl)-1-benzofuran

HRID 365497Notes

Reaction equation

HRID 365497 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][C:22]1[O:26][C:25]2[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=2[CH:23]=1.C(Br)(Br)(Br)[Br:32]>CCOCC>[Br:32][CH2:21][C:22]1[O:26][C:25]2[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=2[CH:23]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 27762631-Benzofuran-2-Ylmethanol

Product 1

HCID 123263162-(Bromomethyl)-1-benzofuran

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
20 °C

Procedure

36.40 g (139 mmol) of triphenylphosphine are added, all at once and with vigorous stirring, to a solution, cooled to 0° C., of 10.40 g (70 mmol) of 2-hydroxymethyl-benzo[b]furan and 46 g (139 mol) of CBr4 in 220 ml of ether. After stirring for 4 hours at 20° C., the precipitate formed is suctioned off and washed with Et2O; the filtrate is dried and concentrated, and the residue is then chromatographed on silica, eluting with a mixture of cyclohexane/CH2Cl2 =80/20, to yield the expected compound in the form of an oil.

Workup

  1. customthe precipitate formed
  2. washwashed with Et2O
  3. customthe filtrate is dried
  4. concentrationconcentrated
  5. customthe residue is then chromatographed on silica
  6. washeluting with a mixture of cyclohexane/CH2Cl2 =80/20

Sources & evidence

ORD record
ord-67e2db7a2c614a93b5e3c1c2ad9f9517
Source dataset
uspto-grants-2000_10
Patent number
US06127396

Reaction notes

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