Dimethylformamide → HCID 86701280, compound

HRID 2290253Notes

Reaction equation

HRID 2290253 reaction equation
[F:1][C:2]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)([F:6])[C:3](O)=[O:4].FC1C=CC(Br)=CC=1.S(Cl)(Cl)=O.CN(C)C=O.Cl.[CH3:32][NH:33][O:34][CH3:35]>O.C(Cl)Cl.N1C=CC=CC=1>[CH3:35][O:34][N:33]([CH3:32])[C:3](=[O:4])[C:2]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)([F:6])[F:1]

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 99931-Bromo-4-fluorobenzeneHCID 24386Thionyl ChlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 20232318Difluoro(4-fluorophenyl)acetic acid

Product 1

HCID 86701280HCID 86701280, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

alpha,alpha-Difluoro-4-fluorophenylacetic acid [1.0 g, prepared from 4-fluorobromobenzene according to the method of Middleton and Bingham, J. Org. Chem., 45, 2883 (1980)] was stirred under nitrogen with thionyl chloride (0.69 g) and dry N,N-dimethylformamide (0.036 g) at room temperature for 15 minutes and then at 70°-75° C. for one hour. The solution was cooled in ice and N,O-dimethylhydroxylamine hydrochloride (0.62 g), dry pyridine (1.5 g) and methylene chloride (15 ml) were added and the mixture stirred at 0° C. for 20 minutes and at room temperature for a further 30 minutes. Water (10 ml) was added and the methylene chloride layer separated. The aqueous phase was extracted with methylene chloride (2×20 ml) and the combined organic extracts were dried over MgSO4 and evaporated. The residue was chromatographed on silica, eluting with methylene chloride to give N-methoxy-N-methyl-alpha,alpha-difluoro-4-fluorophenyl acetamide (1.13 g).

Workup

  1. temperatureThe solution was cooled in ice
  2. customthe methylene chloride layer separated
  3. extractionThe aqueous phase was extracted with methylene chloride (2×20 ml)
  4. dry with materialthe combined organic extracts were dried over MgSO4
  5. customevaporated
  6. customThe residue was chromatographed on silica
  7. washeluting with methylene chloride

Sources & evidence

ORD record
ord-87ac0e9a89e947f4aac8b0b213ac41ca
Source dataset
uspto-grants-1986_10
Patent number
US04616026

Reaction notes

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