Bromine → 2-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-7-bromobenzofuran

HRID 1607256Notes

Reaction equation

HRID 1607256 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH3:20])=[C:14]([OH:21])[C:11]=3[C:12]=2[CH3:13])=[CH:5][CH:4]=1.[Br:24]Br>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2[O:9][C:10]3[C:17]([Br:24])=[CH:16][C:15]([CH2:18][CH2:19][CH3:20])=[C:14]([OH:21])[C:11]=3[C:12]=2[CH3:13])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 145708892-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propylbenzofuran

Product 1

HCID 145797682-(p-Methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-7-bromobenzofuran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(p-methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-benzofuran (1 gm; 3.22mmoles) in methylene chloride (30 mL) was cooled at 0° C. and bromine (0.52 gm; 3.22mmoles) in methylene chloride (10 mL) was added dropwise. The reaction mixture was stirred for 15 minutes. The reaction mixture was washed with a saturated sodium bicarbonate solution, dried (Na2SO4), and concentrated in vacuo. The residue was purified by preparative TLC, eluting with 15% ethylacetate in hexane to yield 2-(p-methoxybenzyl)-3-methyl-4-hydroxy-5-propyl-7-bromobenzofuran, mp. 110°-112° C.

Workup

  1. washThe reaction mixture was washed with a saturated sodium bicarbonate solution
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative TLC
  5. washeluting with 15% ethylacetate in hexane

Sources & evidence

ORD record
ord-d7f63e5d73c24ba4b91a798f76ee32b0
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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