Boron tribromide → Phenol, 4-((2-chloro-5-iodophenyl)methyl)-

HRID 628755Notes

Reaction equation

HRID 628755 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 866988961-Chloro-4-iodo-2-(4-methoxybenzyl)benzene

Product 1

HCID 86698895Phenol, 4-((2-chloro-5-iodophenyl)methyl)-Yield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-chloro-4-iodo-2-(4-methoxybenzyl)benzene (10.0 g, 27.9 mmol) was dissolved in methylene chloride (150 mL). To the resulting mixture was added dropwise boron tribromide (21 g, 83.7 mmol) under cooling in an ice-water bath. After the completion of dropwise addition, the mixture was warmed up to room temperature, and stirred for 3 hr. The mixture was quenched with a saturated sodium bicarbonate solution, was separated into an aqueous phase and an organic phase. The aqueous phase was extracted with methylene chloride (150 mL×2). The organic phases were combined, washed with a saturated sodium chloride solution, dried over anhydrous sodium sulphate, and concentrated under a reduced pressure. The resulting crude product was purified with a silica-gel column chromatography (ethyl acetate:petroleum ether=0-1:20) to produce 8.5 g of a product in a yield of 88%.

Workup

  1. temperatureunder cooling in an ice-water bath
  2. additionAfter the completion of dropwise addition
  3. customThe mixture was quenched with a saturated sodium bicarbonate solution
  4. customwas separated into an aqueous phase
  5. extractionThe aqueous phase was extracted with methylene chloride (150 mL×2)
  6. washwashed with a saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulphate
  8. concentrationconcentrated under a reduced pressure
  9. customThe resulting crude product was purified with a silica-gel column chromatography (ethyl acetate:petroleum ether=0-1:20)

Sources & evidence

ORD record
ord-16f12484f6b9429b91f72350f4d9d671
Source dataset
uspto-grants-2016_04
Patent number
US09315438B2

Reaction notes

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