Methanesulfonic Acid → HCID 11393066, compound

HRID 508665Notes

Reaction equation

HRID 508665 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[C:10]12(O)[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2.CS(O)(=O)=O>C(Cl)Cl.C(Cl)(Cl)Cl>[C:10]12([C:6]3[CH:7]=[C:2]([Br:1])[C:3]([CH3:9])=[CH:4][C:5]=3[OH:8])[CH2:19][CH:14]3[CH2:15][CH:16]([CH2:18][CH:12]([CH2:13]3)[CH2:11]1)[CH2:17]2

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 641521-AdamantanolHCID 728574-Bromo-m-cresol

Product 1

HCID 11393066HCID 11393066, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
54 °C

Procedure

A mixture of 4-bromo-3-methylphenol (4.68 g, 25 mmol), 1-adamantanol (3.81 g, 25 mmol), and MeSO3H (1.2 mL) in CH2Cl2 (18 mL) was stirred and heated at 54° C. (oil-bath) for 28.8 h. The resulting solution was diluted with CHCl3 (150 mL), washed with H2O, 5% NaHCO3, and brine and dried. The residue obtained on concentration was washed with hot hexane to give 6.77 g (85%) of 2-(1-adamantyl)-4-bromo-5-methylphenol as a white solid, mp 155-156° C. IR 3541, 2905, 2845, 1147 cm−1; 1H NMR δ (CDCl3) 1.77 (bs, 6H, AdCH2), 2.07 (bs, 9H, AdCH and AdCH2), 2.28 (s, 3H, CH3), 4.67 (s, 1H, OH), 6.54 (s, 1H, 6-ArH), 7.30 (s, 1H, 3-ArH).

Workup

  1. washwashed with H2O, 5% NaHCO3, and brine
  2. customdried
  3. customThe residue obtained on concentration
  4. washwas washed with hot hexane

Sources & evidence

ORD record
ord-dfd8846045414a4abfc7a8337f7bf883
Source dataset
uspto-grants-2015_08
Patent number
US09096544B2

Reaction notes

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