Triethylamine → [5-tert-Butyl-2-methyl-4-(toluene-4-sulfonylsulfanyl)-phenoxy]-acetic acid

HRID 356521Notes

Reaction equation

HRID 356521 reaction equation
[S:1](Br)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].CCN(CC)CC.C[O:20][C:21](=[O:36])[CH2:22][O:23][C:24]1[CH:29]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:27]([SH:34])=[CH:26][C:25]=1[CH3:35]>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[C:30]([C:28]1[C:27]([S:34][S:1]([C:4]2[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=2)(=[O:3])=[O:2])=[CH:26][C:25]([CH3:35])=[C:24]([CH:29]=1)[O:23][CH2:22][C:21]([OH:36])=[O:20])([CH3:33])([CH3:32])[CH3:31]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 101308854-Methylbenzene-1-sulfonyl bromideHCID 54427811(5-tert-Butyl-4-mercapto-2-methyl-phenoxy)acetic acid methyl ester

Product 1

HCID 18798672[5-tert-Butyl-2-methyl-4-(toluene-4-sulfonylsulfanyl)-phenoxy]-acetic acid

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

1.86 g (7.9 mmol, 2 equivalents) tosyl bromide and 1.05 mL (7.9 mmol) NEt3 were combined in 200 mL CCl4 and the mixture chilled in an ice bath under nitrogen. To this mixture was added a solution of 1.06 g (3.95 mmol) of (5-tert-butyl-4-mercapto-2-methyl-phenoxy)acetic acid methyl ester (prepared in Example MMMM) in 125 mL of CCl4 over 3 hours, and the reaction was allowed to come to ambient temperature overnight. The mixture was then diluted with CH2Cl2, washed with aqueous ammonium chloride and aqueous sodium chloride, and dried (Na2SO4). Concentration gave a residue which was chromatographed on silica gel eluting with 3:1 hexanes:EtOAc to yield the title compound. 1H NMR (CDCl3) δ 1.25 (s, 9 H), 2.14 (s, 3 H), 2.43 (s, 3 H), 3.82 (s, 3 H), 4.68 (s, 2 H), 6.75 (s, 1 H), 7.14 (s, 1 H), 7.25 (d, 2 H), 7.50 (d, 2 H).

Workup

  1. temperaturethe mixture chilled in an ice bath under nitrogen
  2. washwashed with aqueous ammonium chloride and aqueous sodium chloride
  3. dry with materialdried (Na2SO4)
  4. concentrationConcentration
  5. customgave a residue which
  6. customwas chromatographed on silica gel eluting with 3:1 hexanes

Sources & evidence

ORD record
ord-f261841dae6f4b39a4c83a697d2f602a
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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