Thionyl Chloride → HCID 21942520, compound

HRID 82773Notes

Reaction equation

HRID 82773 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([F:12])=[C:7]([CH:11]=1)[C:8](O)=[O:9])#[N:2].S(Cl)([Cl:15])=O>>[F:12][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:11][C:7]=1[C:8]([Cl:15])=[O:9]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 27784625-Cyano-2-fluorobenzoic acid

Product 1

HCID 21942520HCID 21942520, compound

Procedure

A solution of Example 59B (535 mg, 3.24 mmol) in thionyl chloride (3855 mg, 32.4 mmol) was heated at 90° C. for 2 hours. The solution was cooled, concentrated, diluted with toluene, and concentrated to afford 2-fluoro-5-cyanobenzoyl chloride which was used without purification. The title compound was prepared and isolated as described in Example 22B, substituting 2-fluoro-5-cyanobenzoyl chloride for 2-fluoro-5-(trifluoromethyl)benzoyl chloride, in 61% yield. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.33 (s, 9 H) 1.58-1.72 (m, 1H) 1.82 (qd, J=7.01, 6.74 Hz, 2 H) 1.90-1.97 (m, 1 H) 3.61-3.70 (m, 1 H) 3.74-3.83 (m, 1H) 4.24-4.35 (m, 3 H) 7.33 (s, 1 H) 7.52 (dd, J=10.71, 8.72 Hz, 1 H) 8.02-8.07 (m, 1 H) 8.40 (dd, J=6.94, 2.18 Hz, 1 H); MS (DCI/NH3) m/z 388 (M+H)+.

Workup

  1. temperatureThe solution was cooled
  2. concentrationconcentrated
  3. additiondiluted with toluene
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-67352f232c8a44de993beff7d468187b
Source dataset
uspto-grants-2014_09
Patent number
US08846730B2

Reaction notes

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