Toluene → HCID 69928469, compound

HRID 2307550Notes

Reaction equation

HRID 2307550 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Sn](CCCC)(CCCC)CCCC)[CH:12]=2)=[CH:5][C:4]=1[CH2:30][OH:31].Br[C:33]1[CH:41]=[CH:40][C:36]([C:37]([OH:39])=[O:38])=[CH:35][C:34]=1[CH3:42].[Cl-].[NH4+].[C:45]1(C)C=CC=CC=1>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:31][CH2:30][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:3]=1[CH2:2][OH:1])[CH2:9][S:10][C:11]1[CH:12]=[C:13]([C:33]2[CH:41]=[CH:40][C:36]([C:37]([O:39][CH3:45])=[O:38])=[CH:35][C:34]=2[CH3:42])[CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 25517Ammonium ChlorideHCID 821314-Bromo-3-methylbenzoic acidHCID 22606929HCID 22606929, compound

Product 1

HCID 69928469HCID 69928469, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

1.67 g (3 mmol) of [2-hydroxymethyl-5-(3-tributylstannylphenylsulphanylmethyl)phenyl]methanol are dissolved in 30 mL of toluene and 5 mL of DME. 970 mg (4.5 mmol) of 4-bromo-3-methylbenzoic acid are added and the mixture is degassed with a stream of argon for 10 minutes. Pd(PPh3)4 (175 mg, 0.15 mmol) is then added and the reaction medium is brought to reflux and stirred for 24 h. The reaction medium is then treated with ammonium chloride solution and then extracted with ethyl acetate. The organic phases are combined, dried and then concentrated under reduced pressure. The residue is then dissolved in 50 mL of methanol, 1 mL of sulphuric acid is added and the mixture is then refluxed for 18 h. After cooling and treatment with water, the mixture is extracted with ethyl acetate. The organic phases are combined, dried and then concentrated under reduced pressure. The residue is then purified by chromatography on a column of silica. A colourless oil is obtained (m=180 mg, Y=15%).

Workup

  1. customthe mixture is degassed with a stream of argon for 10 minutes
  2. temperatureto reflux
  3. extractionextracted with ethyl acetate
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue is then dissolved in 50 mL of methanol
  7. addition1 mL of sulphuric acid is added
  8. temperaturethe mixture is then refluxed for 18 h
  9. temperatureAfter cooling
  10. extractiontreatment with water, the mixture is extracted with ethyl acetate
  11. customdried
  12. concentrationconcentrated under reduced pressure
  13. customThe residue is then purified by chromatography on a column of silica
  14. customA colourless oil is obtained (m=180 mg, Y=15%)

Sources & evidence

ORD record
ord-7ca71afc5deb4a13a7b5e08dd404a9ac
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

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