Trifluoroacetic acid → (2-Bromophenyl)(2,4,6-trimethoxybenzyl)sulfane

HRID 1987474

Reaction equation

HRID 1987474 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[C:5]([O:11][CH3:12])[C:4]=1[CH2:13]O.[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[SH:22].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22][CH2:13][C:4]1[C:5]([O:11][CH3:12])=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 805982-BromobenzenethiolHCID 516892Sodium BicarbonateHCID 6025152,4,6-Trimethoxybenzyl alcohol

Product 1

HCID 66870845(2-Bromophenyl)(2,4,6-trimethoxybenzyl)sulfaneYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 30.8 g (2,4,6-trimethoxyphenyl)methanol (155.4 mmol) and 29.2 g 2-bromobenzenethiol (155.4 mmol) in 150 ml DCM at 0° C. was added dropwise 1.3 eq TFA. The reaction was stirred 15 minutes at room temperature before saturated NaHCO3 was added until neutral. The organic volatiles were removed under reduced pressure and the aqueous residue was extracted with ethyl acetate (3×150 ml). The organic layer was collected, washed with brine and dried over magnesium sulfate, filtered, and concentrated under reduced pressure afforded a yellowish solid. The solid was washed with ethyl acetate to yield 51.3 g white solid (2-bromophenyl)(2,4,6-trimethoxybenzyl)sulfane (13.9 mmol, 89% yield).

Workup

  1. additionwas added until neutral
  2. customThe organic volatiles were removed under reduced pressure
  3. extractionthe aqueous residue was extracted with ethyl acetate (3×150 ml)
  4. customThe organic layer was collected
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customafforded a yellowish solid
  10. washThe solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-399fea0165bb4c1f8fcb279647e96072
Source dataset
uspto-grants-2009_06
Patent number
US07550505B2

Linked notes

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