Water → 4-((5-Bromo-2-chlorophenyl)methyl)phenol

HRID 628750Notes

Reaction equation

HRID 628750 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16]C)=[CH:12][CH:11]=2)[CH:3]=1.B(Br)(Br)Br.O>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[C:4]([CH:3]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 223285944-Bromo-1-chloro-2-(4-methoxybenzyl)benzene

Product 1

HCID 574237514-((5-Bromo-2-chlorophenyl)methyl)phenolYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-bromo-1-chloro-2-(4-methoxybenzyl)benzene (226 g, 0.73 mol) was dissolved in methylene chloride (2240 mL) under a nitrogen protection and in a protection from light. To the resulting mixture was slowly added dropwise a solution of boron tribromide (357 g, 1.42 mol) in methylene chloride (1416 mL) at −78° C. After the completion of dropwise addition, the reaction mixture was warmed up to room temperature and reacted for 2 hr. TLC indicated the completion of reaction. To the reaction mixture was slowly added dropwise water in an ice-water bath. The methylene chloride phase was collected. The residual aqueous phase was extracted with methylene chloride (1 L) for two times. The organic phases were combined, washed with water for two times and with a saturated sodium chloride solution for one time, dried over anhydrous sodium sulphate, and evaporated by rotation to produce 210 g of a product in a yield of 97%.

Workup

  1. additionAfter the completion of dropwise addition
  2. customreacted for 2 hr
  3. customthe completion of reaction
  4. customThe methylene chloride phase was collected
  5. extractionThe residual aqueous phase was extracted with methylene chloride (1 L) for two times
  6. washwashed with water for two times and with a saturated sodium chloride solution for one time
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated by rotation

Sources & evidence

ORD record
ord-6d9ef829ce284ec29fcd28b6387bf053
Source dataset
uspto-grants-2016_04
Patent number
US09315438B2

Reaction notes

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