tert-Butyl mercaptan → HCID 86662411, compound

HRID 389512Notes

Reaction equation

HRID 389512 reaction equation
[Br:1][C:2]1[C:3](F)=[C:4]([C:7]([F:10])=[CH:8][CH:9]=1)[CH:5]=[O:6].[CH3:12][C:13]([SH:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:3]([S:16][C:13]([CH3:15])([CH3:14])[CH3:12])=[C:4]([C:7]([F:10])=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 6387tert-Butyl mercaptanHCID 11430Potassium CarbonateHCID 221397013-Bromo-2,6-difluorobenzaldehyde

Product 1

HCID 86662411HCID 86662411, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-bromo-2,6-difluorobenzaldehyde (2.00 g, 9.05 mmol), 2-methyl-2-propanethiol (0.917 mL, 8.13 mmol), and potassium carbonate (1.5 g, 11 mmol) in DMF (6 mL) was heated to 50° C. overnight in a sealed tube. The material was extracted with EtOAc, and washed with water (3×). Purification of the organic layer by column chromatography (1 to 2% EtOAc:hexanes) afforded 1.2 g (51%) of the title compound as a yellow solid. 1H NMR (400 MHz, CDCl3): δ 1.34 (s, 9 H), 7.07-7.16 (m, 1 H), 7.91 (dd, J=9.0, 5.2 Hz, 1H), 10.56-10.63 (m, 1 H).

Workup

  1. extractionThe material was extracted with EtOAc
  2. washwashed with water (3×)
  3. customPurification of the organic layer by column chromatography (1 to 2% EtOAc:hexanes)

Sources & evidence

ORD record
ord-bcbf10a71f3845b3b8a9c68b5c7bbbc2
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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