Hydrochloric Acid → HCID 59014506, compound

HRID 1992994Notes

Reaction equation

HRID 1992994 reaction equation
[CH3:1][C:2]1[C:3]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([O:32]C)[CH:27]=2)=[C:4]([O:14][C:15]2[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12]C)=[CH:7][CH:6]=2.B(Br)(Br)Br.C([O-])(O)=O.[Na+].Cl>C(Cl)Cl>[OH:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4]([O:14][C:15]1[CH:20]=[CH:19][C:18](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])=[CH:17][CH:16]=1)=[C:3]([C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=1)[C:2]([CH3:1])=[CH:11]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 68534800HCID 68534800, compound

Product 1

HCID 59014506HCID 59014506, compoundYield 58.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2E)-3-[4-({3-methyl-6-(methyloxy)-2-[3-(methyloxy)phenyl]-1-naphthalenyl}oxy)phenyl]-2-propenoic acid (250) (0.032 g, 0.07 mmol, 1 equiv) in CH2Cl2 (3 mL) at 0° C. was added boron tribromide (0.66 mL, 1.0 M, 9.0 equiv). After 2.5 h, the mixture was treated with saturated aqueous NaHCO3, reacidified to a pH of 2 with 1 M HCl, and extracted with EtOAc (3×5 mL). The pooled organic portions were dried (MgSO4) and concentrated. Radial chromatography (SiO2, 1 mm plate, 70:30; CHCl3/MeOH) furnished the title compound (251) as a pale yellow foam (0.017 g, 57%). 1H NMR (CD3OD, 400 MHz) δ 7.59 (d, J=9.0 Hz, 1H), 7.48 (s, 1H), 7.44-7.36 (m, 1H), 7.29 (d, J=8.2 Hz, 2H), 7.10 (d, J=2.2 Hz, 1H), 7.04 (dd, J=7.5, 7.5 Hz, 1H), 6.94 (dd, J=9.0, 2.2 Hz, 1H), 6.64-6.62 (m, 1H), 6.57-6.55 (m, 4H), 6.39-6.24 (m, 1H), 2.20 (s, 3H). TLC (90:10; CHCl3/MeOH): Rf=0.54.

Workup

  1. extractionextracted with EtOAc (3×5 mL)
  2. dry with materialThe pooled organic portions were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-17cb23d70d8947acb6e1257266a652b0
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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