Ammonium Chloride → (2-Bromophenyl)(3-methoxyphenyl)methanol

HRID 393255

反応式

HRID 393255 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([Mg]Br)[CH:6]=[CH:7][CH:8]=1.[Br:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[O:15].[NH4+].[Cl-]>C1COCC1>[Br:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1)[OH:15]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 811292-BromobenzaldehydeHCID 178490745HCID 178490745、化合物

生成物 1

HCID 22649669(2-Bromophenyl)(3-methoxyphenyl)methanol収率 81%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

3-Methoxyphenyl magnesium bromide (1.0 M solution in THF; 5.4 mL, 5.4 mmol) was taken in a flask under N2 and cooled (0° C.). 2-Bromobenzaldehyde (1 g, 5.4 mmol) in anhydrous THF (10 mL) was added dropwise via syringe over 5 min. The reaction mixture was stirred at this temperature for 20 min. and slowly brought to room temperature. After stirring for another 30 min. satd. NH4Cl solution (20 mL) was added and the mixture was extracted with Et2O (3×25 mL). The combined Et2O extracts were washed with water, brine, dried (MgSO4) and evaporated under reduced pressure to give a yellow oil. The oil was purified by mplc using CH2Cl2 as eluent to give 1.275 g (81%) of the alcohol as a colorless oil. 1H NMR (CDCl3)d: 2.71 (s, 1H, OH), 3.78 (s, 3H, CH3), 6.15 (s, 1H, CH), 6.80-7.58 (m, 8H, Ar—H). 13C NMR (CDCl3)d: 55.80, 75.16, 113.29, 119.90, 123.39, 128.33, 129.11, 129.71, 130.08, 133.39.

後処理

  1. customslowly brought to room temperature
  2. stirringAfter stirring for another 30 min.
  3. extractionthe mixture was extracted with Et2O (3×25 mL)
  4. washThe combined Et2O extracts were washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customto give a yellow oil
  8. customThe oil was purified by mplc

出典と根拠

ORDレコード
ord-8bf2bba6cc7f4e4186e6868ddbe912f7
出典データセット
uspto-grants-2004_10
特許番号
US06806283B2

関連ノート

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