Iodine → 2,6-Dimethoxy-4-methoxymethylphenylboric acid

HRID 347870

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HRID 347870 반응식
[Mg].II.Br[C:5]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([CH2:13][O:14][CH3:15])=[CH:7][C:6]=1[O:16][CH3:17].[B:18]([O:23]C)([O:21]C)[O:19]C.[Cl-].[NH4+]>O1CCCC1.CO>[CH3:17][O:16][C:6]1[CH:7]=[C:8]([CH2:13][O:14][CH3:15])[CH:9]=[C:10]([O:11][CH3:12])[C:5]=1[O:19][B:18]([OH:23])[OH:21]

참가 물질

8

반응물 5

HCID 807IodineHCID 8470Trimethyl borateHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 230809402-Bromo-1,3-dimethoxy-5-(methoxymethyl)benzene

생성물 1

HCID 230809452,6-Dimethoxy-4-methoxymethylphenylboric acid수율 89%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매3회

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온도
70 °C

실험 절차

To a suspension of magnesium turnings (97.5 mg, 4.01 mmol) in tetrahydrofuran (0.5 mL) containing a small amount of added iodine, was added approximately a tenth part of a solution of 2-bromo-1,3-dimethoxy-5-(methoxymethyl)benzene (1.0 g, 3.82 mmol) in tetrahydrofuran (1 mL) under a nitrogen atmosphere, and the mixture was heated in an oil bath at 70° C. The heating was terminated upon gentle reflux of the reaction mixture and fading of the iodine color. To continue the reflux, the remaining solution of 2-bromo-1,3-dimethoxy-5-(methoxymethyl)benzene in tetrahydrofuran was added dropwise to the reaction mixture. Upon completion of the dropwise addition, the reaction mixture was further heated to reflux for 1 hour and then cooled to room temperature. The reaction mixture was then added dropwise to an ice-cooled solution of trimethyl borate (0.57 mL, 4.97 mmol) in tetrahydrofuran (0.5 mL). Upon completion of the dropwise addition and stirring for 40 minutes while cooling with ice, the mixture was stirred overnight at room temperature. An aqueous ammonium chloride solution and methanol were then added to the reaction mixture. Quantitation by liquid chromatography confirmed that the title compound had been obtained at an 89% yield.

후처리

  1. customThe heating was terminated
  2. temperatureupon gentle reflux of the reaction mixture and fading of the iodine color
  3. additionthe remaining solution of 2-bromo-1,3-dimethoxy-5-(methoxymethyl)benzene in tetrahydrofuran was added dropwise to the reaction mixture
  4. additionUpon completion of the dropwise addition
  5. temperaturethe reaction mixture was further heated
  6. temperatureto reflux for 1 hour
  7. temperaturecooled to room temperature
  8. additionThe reaction mixture was then added dropwise to an ice-
  9. additionUpon completion of the dropwise addition
  10. temperaturewhile cooling with ice
  11. stirringthe mixture was stirred overnight at room temperature

출처 및 근거

ORD 기록
ord-b54b18ef27434a6ea3cb26a03f88f82d
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176216B2

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