Hydrochloric Acid → HCID 66652223, compound

HRID 418961Notes

Reaction equation

HRID 418961 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([C:16]3[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=3)[CH:9]3[CH2:15][CH2:14][CH2:13][CH:10]32)=[C:5]([CH2:24]O)[CH:4]=1.B(Br)(Br)[Br:27].C(Cl)Cl.Cl>C(OCC)(=O)C.O>[Br:27][CH2:24][C:5]1[CH:4]=[C:3]([OH:2])[CH:12]=[C:11]2[C:6]=1[CH2:7][CH:8]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)[CH:9]1[CH2:15][CH2:14][CH2:13][CH:10]12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 25134Boron tribromideHCID 66652135HCID 66652135, compound

Product 1

HCID 66652223HCID 66652223, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine [8-Methoxy-4-(4-methoxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalen-6-yl]-methanol (0.025 g, 0.074 mmol), boron tribromide (0.11 g, 0.44 mmol), and methylene chloride (1.5 ml) and stir 3 hours. Add water, ethyl acetate and 1N HCl. Rinse organic layer with water, dry over anhydrous sodium sulfate and remove solvent to yield the titled compound (0.023 g, 84%). 1H NMR (DMSO-d6) 9.18(s, 1H), 9.14 (s, 1H), 7.1 (d, J=7.9 Hz, 2H), 6.7 (d, J=7.9 Hz, 2H), 6.62 (s, 1H), 6.56 (s, 1H), 4.68 (d, J=10.1 Hz, 1H), 4.58 (d, J=9.6 Hz, 1H), 3.4 (m, 1H presumed), 2.95 (m, 1H), 2.8 (m, 2H), 2.45(m, 1H) 2.1 (m, 1H), 1.6-1.1 (m, 5H). MS m/z 371 (M−2).

Workup

  1. dry with materialRinse organic layer with water, dry over anhydrous sodium sulfate
  2. customremove solvent

Sources & evidence

ORD record
ord-cb5c2a15b61549f79d7a45819bd3fe2e
Source dataset
uspto-grants-2012_01
Patent number
US08093302B2

Reaction notes

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