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

HRID 1776400ノート

反応式

HRID 1776400 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8bc24b5d67264f90b0e55a882efef827
出典データセット
uspto-grants-2016_02
特許番号
US09265763B2

反応ノート

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