Boron tribromide → (2E)-3-{4-[(3-Ethyl-6-hydroxy-2-phenyl-1-naphthalenyl)oxy]phenyl}-2-propenoic acid

HRID 1992856Notes

Reaction equation

HRID 1992856 reaction equation
[CH2:1]([C:3]1[C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:5]([O:15][C:16]2[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25])=[CH:18][CH:17]=2)[C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:13]C)=[CH:8][CH:7]=2)[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([C:3]1[C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:5]([O:15][C:16]2[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25])=[CH:18][CH:17]=2)[C:6]2[C:11]([CH:12]=1)=[CH:10][C:9]([OH:13])=[CH:8][CH:7]=2)[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 68537521(2E)-3-(4-{[3-Ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoic acid

Product 1

HCID 11509786(2E)-3-{4-[(3-Ethyl-6-hydroxy-2-phenyl-1-naphthalenyl)oxy]phenyl}-2-propenoic acidYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2E)-3-(4-{[3-ethyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoic acid (60) (104 mg, 0.25 mmol) in reagent grade CH2Cl2 (10 mL) at −10° C. was added BBr3 (1 M in CH2Cl2, 0.74 mL, 0.74 mmol) dropwise. The mixture was then stirred at −5° C. to 0° C. for 2 h, poured into ice water and extracted with EtOAc. The combined organic extract was washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated to give the crude product as reddish brown oil. The crude product was purified by reverse phase preparation HPLC on Agilent 1100 (30% CH3CN in H2O to 100% CH3CN) to give 64 mg (64%) of the title compound (61) as light beige solid. mp 188-190° C. 1H NMR (400 MHz, CH3OH-d4): δ 1.07 (t, J=7.5 Hz, 3H), 2.55 (q, J=7.5 Hz, 2H), 6.26 (d, J=16.0 Hz, 1H), 6.56 (d, J=8.8 Hz, 2H), 6.96 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 7.10-7.16 (m, 3H), 7.18-7.28 (m, 3H), 7.34 (d, J=8.8 Hz, 2H), 7.52 (d, J=16.0 Hz, 1H), 7.53 (s, 1H), 7.59 (d, J=8.9 Hz, 1H). LCMS (ESI): m/z 411 (M+H)+, m/z 409 (M−H)−. HRMS (EI) Calcd for C27H22O4: 411.1596 (M+•). Found: 411.1596.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe combined organic extract
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customto give the crude product as reddish brown oil
  8. customThe crude product was purified by reverse phase preparation HPLC on Agilent 1100 (30% CH3CN in H2O to 100% CH3CN)

Sources & evidence

ORD record
ord-81cbe96e8f1346b084a011ec9df911e9
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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