Water → HCID 21867233, compound

HRID 857151Notes

Reaction equation

HRID 857151 reaction equation
[CH3:1][O:2][C:3](=[O:23])[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([O:19]C)=[C:15]([I:21])[CH:14]=2)=[C:7]([Br:22])[CH:6]=1.B(Br)(Br)Br.O>ClCCl>[Br:11][C:9]1[CH:10]=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:23])[CH:6]=[C:7]([Br:22])[C:8]=1[O:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[C:15]([I:21])[CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 21867266HCID 21867266, compound

Product 1

HCID 21867233HCID 21867233, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

Methyl[3,5-dibromo-4-(4-methoxy-3-iodophenoxy)phenyl]acetate (0.82 g, 1.5 mmol) was dissolved in dichloromethane (25 mL) and cooled down to −78° C. Boron tribromide (8.8 mL, 1 N in dichloromethane) was added and the reaction mixture was stirred at −20° C. for 30 hours. Water was added to the reaction mixture, the organic phase separated and concentrated. The residue was filtered on a short column (silica, dichloromethane/ethyl acetate 1:1), to give 0.73 g (90%) of methyl [3,5-dibromo-4-(4-hydroxy-3-iodophenoxy)-phenyl]acetate as a beige solid mass.

Workup

  1. customthe organic phase separated
  2. concentrationconcentrated
  3. filtrationThe residue was filtered on a short column (silica, dichloromethane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-798e5267059c4a73ab30160ff49dcc6c
Source dataset
uspto-grants-2006_12
Patent number
US07144909B2

Reaction notes

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