Hydrochloric Acid → 4-((5-Bromo-2-chlorothiophen-3-yl)methyl)phenol

HRID 1469175Notes

Reaction equation

HRID 1469175 reaction equation
[Br:1][C:2]1[S:6][C:5]([Cl:7])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=2)[CH:3]=1.B(Br)(Br)Br.Cl.O>C(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([Cl:7])=[C:4]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 25134Boron tribromideHCID 666954545-Bromo-2-chloro-3-(4-methoxybenzyl)thiophene

Product 1

HCID 666909044-((5-Bromo-2-chlorothiophen-3-yl)methyl)phenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of thiophene 3 (5.44 g, 17.1 mmol) in CH2Cl2 (50 mL) was added boron tribromide (20 mL, 1M in CH2Cl2) at 0° C. The mixture was warmed up to room temperature slowly and stirred at room temperature for 3 hours. To the mixture was added aq. 1N HCl solution (35 mL) dropwise at 0° C. and H2O was added to the mixture. The mixture was extracted with EtOAc (50 mL×2). The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude product 4 was dried under high vacuum and used without further purification. (5.1 g, 99%)

Workup

  1. extractionThe mixture was extracted with EtOAc (50 mL×2)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dry with materialThe crude product 4 was dried under high vacuum
  6. customused without further purification

Sources & evidence

ORD record
ord-ef17c04c4f784aca8c18ff3200cb323d
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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