Bromine → HCID 20163666, compound

HRID 256393Notes

Reaction equation

HRID 256393 reaction equation
[CH2:1]([CH:8]1[CH2:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[O:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]Br>C(Cl)(Cl)(Cl)Cl>[CH2:1]([CH:8]1[CH2:12][C:11]2[CH:13]=[C:14]([Br:17])[CH:15]=[CH:16][C:10]=2[O:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 13728724HCID 13728724, compound

Product 1

HCID 20163666HCID 20163666, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

A solution of 2-benzyl-2,3-dihydrobenzofuran (1.9 g, 9 mmole) in 25 ml carbon tetrachloride was cooled to 0° C. and a solution of 0.46 ml (9 mmole) bromine in 5 ml carbon tetrachloride was added at 0° C. The mixture was warmed to room temperature, washed with water, sodium bicarbonate solution, and water again. The solvent was then evaporated to afford 2.5 g of crude product which was purified by column chromatography on silica gel, eluting with hexane to afford 1.0 g (38.5%) of the desired compound, m.p. 70°-72° C.

Workup

  1. washwashed with water, sodium bicarbonate solution, and water again
  2. customThe solvent was then evaporated
  3. customto afford 2.5 g of crude product which
  4. customwas purified by column chromatography on silica gel
  5. washeluting with hexane

Sources & evidence

ORD record
ord-98d67753ae6345bcbb8c688beace6f54
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Reaction notes

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