Triethylamine → HCID 131724678, compound

HRID 2417284Notes

Reaction equation

HRID 2417284 reaction equation
COC(=O)C(Br)C1C=CC=C(Br)C=1.[OH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][CH:22]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Br:33])[CH:28]=2)[C:23]([O:25][CH3:26])=[O:24])=[CH:17][CH:16]=1.C(N(CC)CC)C.S([O-])([O-])=O.[Na+].[Na+].SC1C=CC(O)=CC=1>CO>[CH3:26][O:25][C:23](=[O:24])[CH:22]([S:21][C:18]1[CH:17]=[CH:16][C:15]([OH:14])=[CH:20][CH:19]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Br:33])[CH:28]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24437Sodium SulfiteHCID 2401474-MercaptophenolHCID 131724679HCID 131724679, compound

Product 1

HCID 131724678HCID 131724678, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl[(4hydroxyphenyl)sulfanyl](3-bromophenyl)acetate Methyl bromo(3-bromophenyl)acetate (7.2 g, 23.3 mmol) was added to a stirring solution of triethyl amine (30 ml), sodium sulfite(3.0 g, 23.8 mmol), and 4-mercaptophenol (2.94 g, 23.3 mmol) in methanol (200 ml). The mixture was stirred overnight before it was concentrated and the residue was extracted in ethyl acetate and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated. The compound was isolated using silica-gel column chromatography by eluting it with 20% ethyl acetate: hexane solution. Methyl[(4-hydroxyphenyl) sulfanyl](3-bromophenyl)acetate was isolated as a crude product (8.64 g). MS: 353.0 (M−H)−

Workup

  1. concentrationwas concentrated
  2. extractionthe residue was extracted in ethyl acetate
  3. washwashed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe compound was isolated
  8. washby eluting it with 20% ethyl acetate

Sources & evidence

ORD record
ord-1a10adb30f244f33a5d3e4838a0bd690
Source dataset
uspto-grants-2004_11
Patent number
US06825354B2

Reaction notes

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