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Toluene → HCID 39359537, 화합물

HRID 1626750
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HRID 1626750 반응식
C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:15]1[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=1)[O:18][CH2:19][C:20]([O:22]CC)=[O:21].[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(OCC)(=O)C.CO>[CH3:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[C:15]1[CH:27]=[CH:26][CH:25]=[C:17]([O:18][CH2:19][C:20]([OH:22])=[O:21])[CH:16]=1
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참가 물질

9

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 5197439Ethyl 2-(3-bromophenoxy)acetate

생성물 1

HCID 39359537HCID 39359537, 화합물수율 58.2%

시약·촉매·용매 4

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 887Methanol용매
HCID 962Water용매
HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

Under an Ar atmosphere, 12 mL of toluene, 3 mL of methanol, and 3 mL of 2M aqueous sodium carbonate solution were added to 500 mg (1.93 mmol) of ethyl (3-bromophenoxy)acetate and 352 mg (2.32 mmol) of (2-methoxyphenyl)boronic acid, and the mixture was degassed. Further, 112 mg (0.097 mmol) of tetrakis(triphenylphosphine)palladium(0) was added thereto, and the mixture was heated under stirring at 80° C. for 6 hours. After the mixture was cooled to room temperature, ethyl acetate and water were added thereto to separate the mixture. The water layer was separated, and filtration was performed. Thereafter, acidification was performed with 1N hydrochloric acid, and extraction with ethyl acetate was performed. The organic layer was washed with saturated saline and dried over anhydride magnesium sulfate, followed by filtration and condensation, thereby giving 290 mg of [(2′-methoxybiphenyl-3-yl)oxy]acetic acid (yield: 58%).

후처리

  1. customthe mixture was degassed
  2. temperaturethe mixture was heated
  3. temperatureAfter the mixture was cooled to room temperature
  4. customto separate the mixture
  5. customThe water layer was separated
  6. filtrationfiltration
  7. extractionThereafter, acidification was performed with 1N hydrochloric acid, and extraction with ethyl acetate
  8. washThe organic layer was washed with saturated saline
  9. dry with materialdried over anhydride magnesium sulfate
  10. filtrationfollowed by filtration and condensation

출처 및 근거

ORD 기록
ord-b8613a952c0d4ab0a39a0d825367a162
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785473B2

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