2-Mercaptobenzenemethanol → HCID 58097287, compound

HRID 1514755Notes

Reaction equation

HRID 1514755 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[S:17][CH2:18][CH2:19][O:20][Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])=[N:9][N:10]=2)[CH:7]=1.[SH:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38][OH:39]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:22]([Si:21]([CH:28]([CH3:30])[CH3:29])([CH:25]([CH3:27])[CH3:26])[O:20][CH2:19][CH2:18][S:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:8]1[N:6]2[CH:7]=[C:2]([S:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH2:38][OH:39])[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1)([CH3:24])[CH3:23]

Participants

5

Reactant 2

HCID 1382782-MercaptobenzenemethanolHCID 58097285HCID 58097285, compound

Product 1

HCID 58097287HCID 58097287, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
111 °C

Procedure

To a solution of aryl bromide of Example 7 (50.7 g, 0.10 moles) in toluene (250 ml) was added (2-sulfanylphenyl)methanol (16.8 g, 0.12 moles), sodium (tert)-butoxide (14.4 g, 015 moles) and [1,1′-bis(diphenylphosphino)ferrocene]dichloro palladium (II) (0.41 g, 0.0005 moles). The resultant mixture was sparged with nitrogen for 10 minutes then heated at 111° C. for 16 hours. The reaction was cooled to 20° C., diluted with isopropyl acetate (200 ml) and washed with 2M hydrochloric acid solution (250 ml). The aqueous phase was extracted with isopropyl acetate (50 ml) and the combined organics were washed sequentially with 1M sodium hydroxide solution (250 ml) and 10% w/w sodium chloride solution (250 ml). The solvent was distilled under reduced pressure and replaced with (tert)-butyl methyl ether to give a final volume of 250 ml. The solution was cooled to 5° C. and granulated for 5 hours, then solid was collected by filtration to give the title compound as a white solid (38.5 g, 68%).

Workup

  1. customThe resultant mixture was sparged with nitrogen for 10 minutes
  2. temperatureThe reaction was cooled to 20° C.
  3. additiondiluted with isopropyl acetate (200 ml)
  4. washwashed with 2M hydrochloric acid solution (250 ml)
  5. extractionThe aqueous phase was extracted with isopropyl acetate (50 ml)
  6. washthe combined organics were washed sequentially with 1M sodium hydroxide solution (250 ml) and 10% w/w sodium chloride solution (250 ml)
  7. distillationThe solvent was distilled under reduced pressure
  8. customto give a final volume of 250 ml
  9. temperatureThe solution was cooled to 5° C.
  10. filtrationsolid was collected by filtration

Sources & evidence

ORD record
ord-a30fad94f32647eab0e4f087a2463de6
Source dataset
uspto-grants-2012_07
Patent number
US08222273B2

Reaction notes

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