4-Fluorothiophenol → HCID 21099426, compound

HRID 2376963Notes

Reaction equation

HRID 2376963 reaction equation
C([Li])CCC.[Br-].[F:7][C:8]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:9]=1[CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F:35][C:36]1[CH:41]=[CH:40][C:39]([S:42]([C:45]2[CH:52]=[CH:51][C:48]([CH:49]=O)=[CH:47][CH:46]=2)(=[O:44])=[O:43])=[CH:38][CH:37]=1.FC1C=CC(S)=CC=1>O1CCCC1.C(OCC)(=O)C.O>[F:7][C:8]1[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:9]=1/[CH:10]=[CH:49]/[C:48]1[CH:47]=[CH:46][C:45]([S:42]([C:39]2[CH:40]=[CH:41][C:36]([F:35])=[CH:37][CH:38]=2)(=[O:44])=[O:43])=[CH:52][CH:51]=1

Participants

8

Reactant 4

HCID 677894-FluorothiophenolHCID 12918617HCID 12918617, compoundHCID 21255484HCID 21255484, compoundHCID 178418339Butyllithium

Product 1

HCID 21099426HCID 21099426, compoundYield 22%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Butyllithium (1.6M in hexanes, 0.35 mL, 0.57 mmol) was added dropwise to a cooled (0° C.) suspension of (2,4-difluorobenzyl)triphenylphosphonium bromide (266 mg, 0.57 mmol) in tetrahydrofuran (2.5 mL). The orange suspension was allowed to warm to room temperature for 1 hour. A solution of 4-[(4-fluorophenyl)sulfonyl]benzaldehyde (prepared according to the method of Example 46 Steps 1-4 using 4-fluorobenzenethiol in Step 1, 150 mg, 0.57 mmol) in tetrahydrofuran (0.5 mL) was added and the reaction was stirred overnight at room temperature. Water and ethyl acetate were added and the organic layer was dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 30% ethyl acetate/isohexane, followed by preparative HPLC to give the title compound (46 mg, 22%). 1H NMR δ (ppm)(DMSO): 8.01-7.99 (2H, m), 7.83 (2H, d, J=8.5 Hz), 7.47-7.42 (2H, m), 7.37 (2H, d, J=8.4 Hz), 7.27-7.17 (2H, m), 6.99 (1H, td, J=2.2, 8.6 Hz), 6.82 (1H, d, J=12.3 Hz), 6.70 (1H, d, J=12.0 Hz).

Workup

  1. temperaturea cooled
  2. additionwas added
  3. dry with materialthe organic layer was dried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by flash column chromatography on silica
  6. washeluting with 30% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-d971c0c54eee45bf9964216c309eb8fe
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

Loading…