4-Toluenesulfonyl chloride → HCID 57445087, compound

HRID 558133Notes

Reaction equation

HRID 558133 reaction equation
[OH-].[K+].[Br:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[CH:11](O)[CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C1COCC1.C(Cl)Cl>[Br:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[CH:11]1[CH2:12][N:13]1[C:14]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:20]

Participants

6

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14797Potassium HydroxideHCID 57445088HCID 57445088, compound

Product 1

HCID 57445087HCID 57445087, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Add potassium hydroxide (1.15 g, 17.5 mmol, fresh powder) to a solution of tert-butyl 2-(2-bromo-4-fluorophenyl)-2-hydroxyethylcarbamate (1.19 g, 3.56 mmol) and p-toluenesulfonyl chloride (0.75 g, 3.88 mmol) in dry THF (50 mL). Stir the mixture overnight at RT. Dilute with DCM, and wash with water and aqueous saturated sodium chloride. Dry over sodium sulfate and concentrate. Purify by column chromatography (hexane to 5% ethyl acetate in hexane) to give the title compound as a colorless oil (0.46 g, 41%). 1H NMR (400 MHz, CD3Cl) δ 1.47 (s, 9H), 2.08 (d, J=3.2 Hz, 1H), 2.67 (d, J=5.6 Hz, 1H), 3.59 (dd, J=3.6 Hz, 6.0 Hz, 1H), 7.00 (m, 1H), 7.28 (m, 1H), 7.35 (m, 1H).

Workup

  1. washwash with water and aqueous saturated sodium chloride
  2. dry with materialDry over sodium sulfate
  3. concentrationconcentrate
  4. customPurify by column chromatography (hexane to 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-7ada7ad903fb413bb4b38ef8c728b83b
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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