Water → Benzenemethanol, 4-(difluoromethoxy)-2,6-difluoro-

HRID 1776400노트

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HRID 1776400 반응식
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[C:6]([F:10])[C:7]=1[CH2:8][OH:9].Cl[C:13]([F:18])([F:17])C([O-])=O.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[F:17][CH:13]([F:18])[O:11][C:4]1[CH:3]=[C:2]([F:1])[C:7]([CH2:8][OH:9])=[C:6]([F:10])[CH:5]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2734985Sodium chlorodifluoroacetateHCID 222199753,5-Difluoro-4-(hydroxymethyl)phenol

생성물 1

HCID 69140944Benzenemethanol, 4-(difluoromethoxy)-2,6-difluoro-

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

1 g of 3,5-difluoro-4-(hydroxymethyl)phenol (6.245 mmol, 1 eq.) were dissolved in 16 ml of DMF 1.047 g of sodium chloro(difluoro)acetate (6.87 mmol, 1.1 eq.), 2.442 g of cesium carbonate (7.494 mmol, 1.2 eq.) and 400 μl of water were added. The mixture was stirred at 100° C. bath temperature for 2 hours under nitrogen atmosphere. Then the reaction mixture was partitioned between water and ethyl acetate. The separated aqueous layer was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over a silicone filter and concentrated in vacuo. The residue was purified by flash chromatography to yield 763.3 mg (3.63 mmol, 58.2%) of the analytically pure target compound.

후처리

  1. additionwere added
  2. customThen the reaction mixture was partitioned between water and ethyl acetate
  3. extractionThe separated aqueous layer was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over a silicone
  6. filtrationfilter
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography
  9. customto yield 763.3 mg (3.63 mmol, 58.2%) of the analytically pure target compound

출처 및 근거

ORD 기록
ord-8bc24b5d67264f90b0e55a882efef827
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265763B2

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