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

HRID 393255

반응식

HRID 393255 반응식
[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]

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 811292-BromobenzaldehydeHCID 178490745HCID 178490745, 화합물

생성물 1

HCID 22649669(2-Bromophenyl)(3-methoxyphenyl)methanol수율 81%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8bf2bba6cc7f4e4186e6868ddbe912f7
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06806283B2

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