Water → 4-Fluorophenylacetyl chloride

HRID 51283

반응식

HRID 51283 반응식
O.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.CN(C)C=O.C(Cl)(=O)C([Cl:21])=O>C1(C)C=CC=CC=1>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([Cl:21])=[O:12])=[CH:5][CH:4]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6228DimethylformamideHCID 98372-(4-Fluorophenyl)acetic acidHCID 65578Oxalyl chloride

생성물 1

HCID 37449884-Fluorophenylacetyl chloride수율 90%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Into a 1-L three-neck flask equipped with a mechanical stirrer, an addition funnel, and a nitrogen bubbler vented to a water scrubber was placed 60.0 g (0.389 mol) of 4-fluorophenylacetic acid, 0.18 g, 0.002 mol) of N,N-dimethylformamide and 250 g of toluene. The addition funnel was charged with 50.4 g (0.397 mol) of oxalyl chloride and added to the reaction mixture over a 10 minute period resulting in gas evolution (4.7° C. exotherm was observed). The reaction mixture was stirred at ambient temperature for 2.5 hours (gas evolution complete) and the head space of the reaction flask was sparged with nitrogen for 10 minutes before storing the material. HPLC assay of the solution indicated that 19.1 wt % of the solution was 4-fluoroacetyl chloride, thus affording a 99% yield. Purification of crude 4-fluorophenylacetyl chloride by vacuum distillation (57-58° C., 0.15 mm Hg) affords 4-fluorophenylacetyl chloride as a clear liquid in 90% yield.

후처리

  1. customInto a 1-L three-neck flask equipped with a mechanical stirrer, an addition funnel
  2. additionadded to the reaction mixture over a 10 minute period
  3. customresulting in gas evolution (4.7° C. exotherm was observed)
  4. customthe head space of the reaction flask was sparged with nitrogen for 10 minutes
  5. customthus affording a 99% yield
  6. customPurification of crude 4-fluorophenylacetyl chloride
  7. distillationby vacuum distillation (57-58° C., 0.15 mm Hg)

출처 및 근거

ORD 기록
ord-0c4f4e2a8198473380d2926977b08b20
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713627B2

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