Methanesulfonic Acid → HCID 85724205, compound

HRID 508672Notes

Reaction equation

HRID 508672 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.[C:11]12(O)[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2.CS(O)(=O)=O>C(Cl)Cl>[C:11]12([C:6]3[CH:7]=[C:2]([Br:1])[CH:3]=[C:4]([O:9][CH3:10])[C:5]=3[OH:8])[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]3)[CH2:12]1)[CH2:18]2

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 641521-AdamantanolHCID 2622344-Bromo-2-methoxyphenol

Product 1

HCID 85724205HCID 85724205, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
54 °C

Procedure

A mixture of 4-bromo-2-methoxyphenol (2.00 g, 9.85 mmol), 1-adamantanol (1.50 g, 9.85 mmol), and MeSO3H (0.8 mL) in CH2Cl2 (8 mL) was stirred with heating at 54° C. (oil-bath) for 18.3 h. The resulting solution was quenched with H2O (30 mL) and extracted with EtOAc (120 mL). The extract was washed with 5% NaHCO3 and brine and dried. The residue obtained on concentration was purified on silica gel (4% EtOAc/hexane) to give 2.5 g (76%) of 2-(1-adamantyl)-4-bromo-6-methoxyphenol as a white solid, mp 157-159° C. IR 3510, 2903, 2850, 1413, 1217 cm−1; 1H NMR δ (CDCl3) 1.76 (bs, 6H, AdCH2), 2.07 (bs, 9H, AdCH and AdCH2), 3.87 (s, 3H, OCH3), 5.90 (s, 1H, OH), 6.86 (d, J=2.4 Hz, 1H, 5-ArH), 6.95 ppm (d, J=2.4 Hz, 1H, 3-ArH).

Workup

  1. customThe resulting solution was quenched with H2O (30 mL)
  2. extractionextracted with EtOAc (120 mL)
  3. washThe extract was washed with 5% NaHCO3 and brine
  4. customdried
  5. customThe residue obtained on concentration
  6. customwas purified on silica gel (4% EtOAc/hexane)

Sources & evidence

ORD record
ord-341ff4c92bb14723a6cd72fd6adf381a
Source dataset
uspto-grants-2015_08
Patent number
US09096544B2

Reaction notes

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