Pyridine → Toluene-4-thiosulfonic acid S-(2-tert-butyl-4-hydroxy-5-methyl-phenyl) ester

HRID 1003863Notes

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].N1C=CC=CC=1.[C:18]([C:22]1[C:23]([SH:30])=[CH:24][C:25]([CH3:29])=[C:26]([OH:28])[CH:27]=1)([CH3:21])([CH3:20])[CH3:19]>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl>[C:18]([C:22]1[CH:27]=[C:26]([OH:28])[C:25]([CH3:29])=[CH:24][C:23]=1[S:30][S:1]([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2])([CH3:21])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 0 °C

Procedure

To a round bottom flask equipped with a magnetic stirrer and addition funnel were added tosyl bromide (30.6 g, 130 mmol), CCl4 (150 mL), and pyridine (10.51 mL, 130 mmol), respectively. This slurry was cooled to 0° C. and treated dropwise a solution of 24.3 g (124 mmol) of 5-tert-butyl-4-mercapto-2-methyl-phenol (prepared in Example QQQ) in CCl4 (150 mL). The mixture was diluted with CHCl3, washed with brine, and dried (MgSO4). The solvent was evaporated to give a solid which was washed and filtered with hexanes:Et2O (4:1) to give the title compound. 1H NMR (CDCl3) δ 1.22 (s, 9 H), 2.11 (s, 3 H), 2.42 (s, 3 H), 6.87 (s, 1 H), 7.16 (s, 1 H) 7.26 (d, 2 H), 7.49 (d, 2 H).

Workup

customTo a round bottom flask equipped with a magnetic stirrer and addition funnel
washwashed with brine
dry with materialdried (MgSO4)
customThe solvent was evaporated
customto give a solid which
washwas washed
filtrationfiltered with hexanes:Et2O (4:1)

Sources & evidence

ORD record: ord-9c1666417a4d410d8f7e0bd950ec50b7
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06046355

Reaction notes

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