Boron tribromide → 2-{4-[2-(3,4-Dihydroxy-phenyl)-ethyl]-phenylamino}-benzoic acid

HRID 488489Notes

Reaction equation

HRID 488489 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=3[C:22]([OH:24])=[O:23])=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[O:9]C.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20]3[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=3[C:22]([OH:24])=[O:23])=[CH:15][CH:14]=2)[CH:6]=[CH:7][C:8]=1[OH:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 9951634HCID 9951634, compound

Product 1

HCID 222697052-{4-[2-(3,4-Dihydroxy-phenyl)-ethyl]-phenylamino}-benzoic acidYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{4-[2-(3,4-dimethoxy-phenyl)-ethyl]phenylamino}-benzoic acid (0.28 g, 0.74 mmol) in CH2Cl2 (20 mL), BBr3 (3.5 mL, 1M in CH2Cl2, 3.5 mmol) was added at room temperature under a N2 atmosphere. The reaction mixture was allowed to stir at room temperature for 2 hours and then poured into ice water (50 mL). This mixture was extracted with EtOAc, and the organic layer was washed two times with water, dried (Na2SO4), filtered and concentrated in vacuo to yield 0.24 g (0.69 mmol, 93%) of the desired product. mp 215-217° C.

Workup

  1. extractionThis mixture was extracted with EtOAc
  2. washthe organic layer was washed two times with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-73bb319c97c144d9bc1064ae74d40b8c
Source dataset
uspto-grants-2005_12
Patent number
US06972287B1

Reaction notes

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