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

HRID 2097477ノート

反応式

HRID 2097477 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 666028231-Bromo-3-cyclopropylmethoxy-4-difluoromethoxy-2-iodobenzene収率 92.1%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒

実験手順

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%)

後処理

  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

出典と根拠

ORDレコード
ord-6301fb8ea07044d18c6d3144ca58b20b
出典データセット
uspto-grants-2013_05
特許番号
US08450319B2

反応ノート

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