Potassium Carbonate → 1-Benzyl-4-chloro-2-methoxybenzene

HRID 272744ノート

反応式

HRID 272744 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[O:10][CH3:11].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:2]([C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[O:10][CH3:11])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 223274741-(Bromomethyl)-4-chloro-2-methoxybenzene

生成物 1

HCID 692167101-Benzyl-4-chloro-2-methoxybenzene収率 18.4%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

1-Bromomethyl-4-chloro-2-methoxy-benzene (50 mg, 0.21 mmol), phenyl boronic acid (28 mg, 0.23 mmol), Pd(PPh3)4 (24 mg, 0.021 mmol) and K2CO3 (87 mg, 0.63 mmol) were combined in dioxane, purged with N2, and heated to reflux for 16 hours. The mixture was then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel eluting with 4:1 hexanes/ethyl acetate to provide 9 mg (18%) of the title compound. MS (ESI) m/e 233 (M+H)+.

後処理

  1. custompurged with N2
  2. temperatureheated
  3. temperatureto reflux for 16 hours
  4. customThe mixture was then partitioned between ethyl acetate and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe residue was purified by flash column chromatography on silica gel eluting with 4:1 hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-cd67fa8b66294287b5b57e87a2dce8c8
出典データセット
uspto-grants-2008_11
特許番号
US07456169B2

反応ノート

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