1,3-Dibromopropane → 2-[4-(3-Bromopropoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 657527ノート

反応式

HRID 657527 の反応式
[CH3:1][C:2]1([CH3:16])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[O:3]1.C([O-])([O-])=O.[K+].[K+].[Br:23][CH2:24][CH2:25][CH2:26]Br>CC#N>[Br:23][CH2:24][CH2:25][CH2:26][O:15][C:12]1[CH:13]=[CH:14][C:9]([B:4]2[O:3][C:2]([CH3:16])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]2)=[CH:10][CH:11]=1

参加物

5

反応物 3

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 27346244-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

生成物 1

HCID 441197642-[4-(3-Bromopropoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane収率 86.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

4-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (CAS #269409-70-3) (10.5 g, 47 mmol) was dissolved in dry CH3CN (200 mL) and dry, pulverized K2CO3 (10.4 g, 75 mmol) was introduced. 1,3-dibromopropane (38.1 mL, 375 mmol) was added dropwise, and the reaction mixture was heated at 70° C. for 7 h under a nitrogen atmosphere. The cooled reaction mixture was filtered and the filtrate was evaporated to an oily residue, which was applied to a column of silica gel. Elution initially with hexanes, gradually increasing polarity to a mixture of hexanes/ethyl acetate (25:1, 20:1 and 10:1) as eluent, provided the title compound (13.93 g, 86%) which crystallized on standing to a white solid, m.p. 62-65° C.

後処理

  1. customdry
  2. additionwas introduced
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. customthe filtrate was evaporated to an oily residue, which
  6. washElution initially with hexanes
  7. temperaturegradually increasing polarity
  8. additionto a mixture of hexanes/ethyl acetate (25:1, 20:1 and 10:1) as eluent

出典と根拠

ORDレコード
ord-4c7e820adb7641b0bc25cf47346d48be
出典データセット
uspto-grants-2011_12
特許番号
US08076331B2

反応ノート

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