Hydrochloric Acid → (3,5-Dibromo-4-methylphenyl)methanol

HRID 1667508ノート

反応式

HRID 1667508 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Br:13])[C:11]=1[CH3:12])[C:5](OC)=[O:6].[BH4-].[Na+].Cl>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:9]=[C:10]([Br:13])[C:11]=1[CH3:12]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 624016Methyl 3,5-dibromo-4-methylbenzoateHCID 4311764Sodium borohydride

生成物 1

HCID 60156325(3,5-Dibromo-4-methylphenyl)methanol収率 72.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of methyl 3,5-dibromo-4-methylbenzoate (15 g, 48.706 mmol), NaBH4 (5.53 g, 146.18 mmol) and absolute ethanol (175 mL) was heated to reflux for 4 h. The mixture was cooled, followed by acidification with 2N HCl. The solids were filtered through celite and rinsed with EtOAc. The filtrate was poured onto water and extracted. The organic layer was washed with brine and dried (Na2SO4). Chromatography (Hexanes/EtOAc) afforded (3,5-dibromo-4-methyl-phenyl)-methanol (9.94 g) as a white solid. 1H NMR (400 MHz, d6-DMSO) δ: 2.48 (s, 3H), 4.45 (d, 2H), 5.38 (t, 1H), 7.57 (s, 2H) ppm.

後処理

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. temperatureThe mixture was cooled
  4. filtrationThe solids were filtered through celite
  5. washrinsed with EtOAc
  6. additionThe filtrate was poured onto water
  7. extractionextracted
  8. washThe organic layer was washed with brine
  9. dry with materialdried (Na2SO4)

出典と根拠

ORDレコード
ord-4f30819e3f114251b81fcbc8592ced18
出典データセット
uspto-grants-2011_10
特許番号
US08044041B2

反応ノート

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