Water → 4-{[(3-Chloro-4-hydroxyphenyl)thio]methyl}benzaldehyde

HRID 68231Notes

Reaction equation

HRID 68231 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[C:13]([SH:15])[CH:12]=[CH:11][C:10]=1[OH:16].Br[CH2:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1.O>O1CCOCC1>[Cl:8][C:9]1[CH:14]=[C:13]([S:15][CH2:18][C:19]2[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=2)[CH:12]=[CH:11][C:10]=1[OH:16]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 112064214-(Bromomethyl)benzaldehydeHCID 143697432-Chloro-4-mercaptophenol

Product 1

HCID 578598114-{[(3-Chloro-4-hydroxyphenyl)thio]methyl}benzaldehydeYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Triethylamine (5.0 mL, 35.9 mmol) was added dropwise to a solution of 2-chloro-4-mercaptophenol (3.60 g, 22.4 mmol) and 4-bromomethyl benzaldehyde (3.93 g, 19.7 mmol) in dioxane (150 mL) at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 20 hours. Water (100 mL) was added to the reaction mixture and it was then partitioned with ethyl acetate and brine (200 mL each). The aqueous layer was re-extracted with ethyl acetate (100 mL). The combined organic layers were dried over sodium sulphate and concentrated in vacuo affording a yellow solid. This was purified by trituration with acetonitrile (5 mL/g) for 30 minutes. After filtration this afforded a light yellow solid as the pure product, 84% yield, 5.27 g.

Workup

  1. customwas then partitioned with ethyl acetate and brine (200 mL each)
  2. extractionThe aqueous layer was re-extracted with ethyl acetate (100 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulphate
  4. concentrationconcentrated in vacuo
  5. customaffording a yellow solid
  6. customThis was purified by trituration with acetonitrile (5 mL/g) for 30 minutes
  7. filtrationAfter filtration
  8. customthis afforded a light yellow solid as the pure product, 84% yield, 5.27 g

Sources & evidence

ORD record
ord-baf0fbcee31e48baaab346ce0d70e562
Source dataset
uspto-grants-2014_09
Patent number
US08822439B2

Reaction notes

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