Water → HCID 11589327, compound

HRID 1992816Notes

Reaction equation

HRID 1992816 reaction equation
[CH3:1][C:2]1[C:3]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][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.O>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:16]=[CH:17][C:18](/[CH:21]=[CH:22]/[C:23]([OH:25])=[O:24])=[CH:19][CH:20]=1)=[C:3]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:2]([CH3:1])=[CH:11]2

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 68534631HCID 68534631, compound

Product 1

HCID 11589327HCID 11589327, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (5° C.) solution of (2E)-3-(4-{[3-methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}phenyl)-2-propenoic acid (10) (1.10 g, 2.68 mmol) in CH2Cl2 (60 mL) was added BBr3 (0.8 mL, 8 mmol) slowly. The reaction mixture was stirred between 5° C. and 20° C. for 1 h and poured into water (150 mL) slowly. The layers were separated and the aqueous layer was further extracted with EtOAc (3×150 mL). The combined organic layer was washed with brine (1×100 mL) dried (Na2SO4) and concentrated to afford the crude product. Purification by flash column chromatography on silica gel using CHCl3:MeOH as an eluent, gave 0.88 g (83%) of the title compound as an off-white solid. IR (film): 30.58, 1682, 1632, 1599, 1504, 1227, 1165 cm−1. 1H NMR (400 MHz, MeOH-d4): δ 7.60 (d, J=8.8 Hz, 1H), 7.51 (s, 1H), 7.52 (d, J=16.0 Hz, 1H), 7.33 (d, J=8.8 Hz, 2H), 7.27-7.20 (m, 3H), 7.14-11 (m, 3H), 6.96 and 6.94 (dd, J1=9.2 Hz, J2=2.4 Hz, 1H), 6.57 (d, J=8.4 Hz, 2H), 6.75 (d, J=16.0 Hz, 1H), 2.19 (s, 3H). 13C NMR (100 MHz, MeOH-d4): δ 169.5, 161.3, 156.1, 147.1, 144.78, 136.82, 136.3, 135.9, 130.3, 129.8, 129.5, 127.8, 126.83, 124.0, 123.9, 120.9, 118.1, 115.8, 115.7, 108.6, 20.32. HRMS Calcd for C26H20O4: 397.1440. Found: 397.1439.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was further extracted with EtOAc (3×150 mL)
  3. washThe combined organic layer was washed with brine (1×100 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto afford the crude product
  7. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-34e7f6658ffa4b13853e30ac61fa5281
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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