Bromine → HCID 12112125, compound

HRID 1793207Notes

Reaction equation

HRID 1793207 reaction equation
[CH3:1][C:2]1[C:13]([O:14]C2CCCCO2)=[CH:12][C:5]2[CH:6]=[C:7]([C:9](=[O:11])[CH3:10])[O:8][C:4]=2[C:3]=1[CH3:21].[Br:22]Br>C(Cl)(Cl)Cl>[Br:22][C:6]1[C:5]2[CH:12]=[C:13]([OH:14])[C:2]([CH3:1])=[C:3]([CH3:21])[C:4]=2[O:8][C:7]=1[C:9](=[O:11])[CH3:10]

Participants

4

Reactant 2

HCID 24408BromineHCID 22026140HCID 22026140, compound

Product 1

HCID 12112125HCID 12112125, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-[6,7-dimethyl-5-(tetrahydro-pyran-2-yloxy)-benzofuran-2-yl]-ethanone (200 mg) in chloroform (20 mL) was added bromine (120 mg). After 1 h, the solution was washed with water and dried over MgSO4 and concentrated. The residue was purified by silica gel column eluting with 10% hexane in DCM to give 1-(3-Bromo-5-hydroxy-6,7-dimethyl-benzofuran-2-yl)-ethanone, as a yellow solid. 1H NMR (CDCl3, 300 MHz) δ: 7.38(s, 1H), 5.55 (s, 1H, OH), 2.60, 2.50, 2.31 (3 s, 9H) ppm. MS (m/z): 283, 285 (M+H+).

Workup

  1. washthe solution was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column
  5. washeluting with 10% hexane in DCM

Sources & evidence

ORD record
ord-3d4f7692cf52494abd0a18c6db39fe8c
Source dataset
uspto-grants-2006_07
Patent number
US07078541B2

Reaction notes

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