Water → HCID 67041909, compound

HRID 62761Notes

Reaction equation

HRID 62761 reaction equation
[Cl:1][C:2]1[C:7]([O:8]C)=[CH:6][C:5]([I:10])=[CH:4][C:3]=1[O:11]C.B(Br)(Br)Br.O>C(Cl)Cl>[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([I:10])=[CH:4][C:3]=1[OH:11]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 670417372-Chloro-5-iodo-1,3-dimethoxybenzene

Product 1

HCID 67041909HCID 67041909, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-chloro-5-iodo-1,3-dimethoxybenzene (3) (7.15 g, 23.9 mmol) in DCM (20 mL) was cooled to 0° C. Boron tribromide (11.3 mL, 120 mmol) was added dropwise over 30 min and the reaction mixture was allowed to slowly warm to RT and stirred for 20 h. The reaction mixture was cautiously added to iced water (30 mL) with stirring. The phases were separated and the organic solution was washed with brine (3×30 mL). The solvent was removed in vacuo to afford 2-chloro-5-iodobenzene-1,3-diol (4) (4.17 g, 64% yield) as a white solid: m/z 269 [M−H]− (ES−).

Workup

  1. stirringwith stirring
  2. customThe phases were separated
  3. washthe organic solution was washed with brine (3×30 mL)
  4. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-34edaf893ef8428083881c8409145608
Source dataset
uspto-grants-2016_09
Patent number
US09447028B2

Reaction notes

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