Boron tribromide → 4-Ethyl-3-hydroxybenzoic acid

HRID 1158442Notes

Reaction equation

HRID 1158442 reaction equation
[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[O:12]CCCOC)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[OH:12])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 573555384-Ethyl-3-(3-methoxypropoxy)benzoic acid

Product 1

HCID 215064424-Ethyl-3-hydroxybenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-ethyl-3-(3-methoxy-propoxy)-benzoic acid (6.44 g, 27.03 mmol) in CH2Cl2 (150 mL) at −78° C. is slowly added BBr3 (9 mL, 93.41 mmol). The reaction mixture is allowed to reach RT and stirred for 3 hours, then poured into ice/water and filtrated to afford the title product as a white solid. TLC, Rf (CH2Cl2/MeOH 95:5)=0.2.

Workup

  1. customat −78° C.
  2. customto reach RT
  3. filtrationfiltrated

Sources & evidence

ORD record
ord-d76ef5728a66498ba1ebf12bd22f6729
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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