Water → HCID 10125597, compound

HRID 2086127Notes

Reaction equation

HRID 2086127 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:7]([CH:25]=1)=[C:8]([CH2:22][CH2:23][CH3:24])[CH:9]=[C:10]1[C:15]=2[O:14][CH2:13][C:12]2[CH:16]=[C:17]([O:20]C)[CH:18]=[CH:19][C:11]1=2.B(Br)(Br)Br.O>C(Cl)Cl>[CH2:22]([C:8]1[CH:9]=[C:10]2[C:15](=[C:6]3[CH:5]=[CH:4][C:3]([OH:2])=[CH:25][C:7]=13)[O:14][CH2:13][C:12]1[CH:16]=[C:17]([OH:20])[CH:18]=[CH:19][C:11]2=1)[CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 22728209HCID 22728209, compound

Product 1

HCID 10125597HCID 10125597, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 2,8-dimethoxy-12-propyl-6H-dibenzo[c,h]chromene (220 mg, 0.658 mmoles) in CH2Cl2 (33 ml) at 0° C. was slowly added boron tribromide (3.95 ml of 1 N solution in CH2Cl2, 3.95 mmols). The reaction mixture was stirred at 0° C. for 3 h. 4 ml water was injected into the mixture with stirring in an ice-water bath. CH2Cl2 in the mixture was removed under reduced pressure. The resulting mixture was extracted with ethyl acetate (x3). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and stripped of solvent to give 120 mg (60%) of the title compound as white solid. The analytical sample was obtained by purification with silica column chromatography (20%-30% ethyl acetate—hexane) and then recrystalliazation with ethyl acetate—hexane: mp 86-95° C.; 1H NMR (DMSO-d6): δ 1.00 (3H, t, J=7.24 Hz), 1.63-1.76 (2H, m), 2.87 (2H, t, J=7.22 Hz), 5.16 (2H, s), 6.69 (1H, d, J=2.28 Hz), 6.79 (1H, dd, J=8.39 Hz, J=2.28 Hz), 7.03 (1H, dd, J=9.02 Hz, J=2.18 Hz), 7.20 (1H, d, J=2.10 Hz), 7.60 (1H, s), 7.62 (1H, d, J=7.85 Hz), 7.99 (1H, d, J=9.01 Hz), 9.61 (1H, s), 7.76 (1H, s); MS (ESI) m/z 305 (M−H)−, 307 (M+H)+; HRMS: calcd for C20H18O3, 306.1256; found (ESI),305.11827.

Workup

  1. stirringwith stirring in an ice-water bath
  2. customCH2Cl2 in the mixture was removed under reduced pressure
  3. extractionThe resulting mixture was extracted with ethyl acetate (x3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-098c2a81d7244ff6a2cdc773a669dddd
Source dataset
uspto-grants-2004_04
Patent number
US06723747B2

Reaction notes

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