Methanesulfonic Acid → HCID 87310593, compound

HRID 508675Notes

Reaction equation

HRID 508675 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.O[C:10]12[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([C:13]3=[O:20])[CH2:11]1)[CH2:17]2.CS(O)(=O)=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:16]23[CH2:18][CH:12]4[CH2:11][CH:10]([CH2:19][CH:14]([C:13]4=[O:20])[CH2:15]2)[CH2:17]3)[CH:3]=1

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 78084-BromophenolHCID 64184Idramantone

Product 1

HCID 87310593HCID 87310593, compoundYield 79%

Conditions

Temperature
80 °C

Procedure

The mixture of 4-bromophenol (3.11 g, 17.98 mmol), 5-hydroxy-2-adamantanone (2.49 g, 14.98 mmol), and MeSO3H (7 mL) was stirred with heating at 80° C. (oil-bath) for 5 h. The resulting mixture was quenched with H2O (40 mL) and filtered. The precipitate was washed several times with H2O, 5% NaHCO3, and CH2Cl2 and dried to give 3.76 g (79%) of 5-(5′-bromo-2′-hydroxyphenyl)-2-adamantanone as a white solid, mp 287-289° C. 1H NMR 8 (DMSO-d6) 1.82-2.45 (m, 13H, AdCH and AdCH2), 6.71 (d, J=8.5 Hz, 1H, 3′-ArH), 7.10 (d, J=2.4 Hz, 1H, 4′-ArH), 7.16 (dd, J=2.4 Hz, 8.5 Hz, 1H, 6′-ArH), 9.78 (s, 1H, OH).

Workup

  1. customThe resulting mixture was quenched with H2O (40 mL)
  2. filtrationfiltered
  3. washThe precipitate was washed several times with H2O, 5% NaHCO3, and CH2Cl2
  4. customdried

Sources & evidence

ORD record
ord-5979c2c346a34b73b8d733931c405056
Source dataset
uspto-grants-2015_08
Patent number
US09096544B2

Reaction notes

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