p-Toluenesulfonic acid monohydrate → HCID 10826647, compound

HRID 1910998Notes

Reaction equation

HRID 1910998 reaction equation
[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[CH2:6][CH2:7][CH2:8][CH:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10](O)[C:4]=2[CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:17]=[CH:16][C:5]2[CH2:6][CH2:7][CH2:8][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 71061027HCID 71061027, compound

Product 1

HCID 10826647HCID 10826647, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of methyl 3-bromo-5-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulene-6-carboxylate from step A3 (230 mg, 0.769 mmol) in toluene (3 mL) was added p-toluenesulfonic acid monohydrate (29.2 mg, 0.154 mmol). The mixture was heated at reflux for 4 h. The solvent was removed in vacuo, and the residue was purified using silica gel column chromatography (hexanes-10% EtOAc) to give methyl 2-bromo-6,7-dihydro-5H-benzo[7]annulene-8-carboxylate (175 mg, 0.622 mmol, 81% yield). 1H NMR (500 MHz, chloroform-d) δ 7.61 (s, 1H), 7.44 (d, J=1.8 Hz, 1H), 7.32 (dd, J=8.1, 2.0 Hz, 1H), 7.02 (d, J=7.9 Hz, 1H), 3.83 (s, 3H), 2.79-2.72 (m, 2H), 2.63 (t, J=6.6 Hz, 2H), 2.09-2.00 (m, 2H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 4 h
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified

Sources & evidence

ORD record
ord-407bbcae37584336919b9318450076ed
Source dataset
uspto-grants-2013_12
Patent number
US08604024B2

Reaction notes

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