Hydrochloric Acid → 1-Bromo-3-cyclopropylmethoxy-4-difluoromethoxy-2-iodobenzene

HRID 2097477노트

반응식

HRID 2097477 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH2:10][CH:11]2[CH2:13][CH2:12]2)[C:3]=1[I:14].[OH-].[Na+].Cl[CH:18]([F:20])[F:19].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:18]([F:20])[F:19])=[C:4]([O:9][CH2:10][CH:11]2[CH2:13][CH2:12]2)[C:3]=1[I:14]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 6372ChlorodifluoromethaneHCID 14798Sodium HydroxideHCID 575717094-Bromo-2-cyclopropylmethoxy-3-iodophenol

생성물 1

HCID 666028231-Bromo-3-cyclopropylmethoxy-4-difluoromethoxy-2-iodobenzene수율 92.1%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매

실험 절차

To 20 ml of toluene solution containing 1.84 g (5.0 mmol) of 4-bromo-2-cyclopropylmethoxy-3-iodophenol obtained in Reference example 12-(d) were added 0.8 g (2.5 mmol) of tetrabutylammonium bromide and 10 ml of 35% aqueous solution of sodium hydroxide, and then, 5.0 g (62 mmol) of chlorodifluoromethane was blown thereinto at 80° C. over 30 minutes. After completion of the reaction, 2N hydrochloric acid was added to the reaction mixture to adjust a pH thereof to 5. The organic layer after separation was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The obtained residue was applied to silica gel column chromatography (Eluent; hexane:ethyl acetate=9:1 (V/V)), and the fractions containing the desired compound were concentrated under reduced pressure to obtain 1.93 g of the title compound as a colorless oil. (Yield: 92%)

후처리

  1. additionwas added to the reaction mixture
  2. customThe organic layer after separation
  3. washwas washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionthe fractions containing the desired compound
  7. concentrationwere concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6301fb8ea07044d18c6d3144ca58b20b
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450319B2

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