Hydrochloric Acid → 2-[(1-tert-Butyl)-1H-tetrazol-5-yl]phenylboronic acid

HRID 1440454ノート

反応式

HRID 1440454 の反応式
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2Br)=[N:8][N:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[B:17](OC(C)C)([O:22]C(C)C)[O:18]C(C)C.Cl>C1COCC1.BrCCBr>[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[B:17]([OH:22])[OH:18])=[N:8][N:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 218408841-tert-Butyl-5-(2-bromophenyl)-1H-tetrazole

生成物 1

HCID 109447112-[(1-tert-Butyl)-1H-tetrazol-5-yl]phenylboronic acid収率 48%

試薬・触媒・溶媒 2

HCID 78391,2-Dibromoethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To dry Mg turnings (76 mg, 3.13 mmol) in THF (1 mL) was added a solution of 1-tert-butyl-5-(2-bromophenyl)-1H-tetrazole (733 mg, 2.61 mmol) in THF (1.5 mL), 1,2-Dibromoethane (20 mL) was added and the mixture was warmed slightly with a heat gun. After 5 min, triisopropyl borate (564 mg, 3.00 mmol) was added and the mixture was stirred at room temperature for 23 h. Ice and 0.5 N HCl (7 mL) were added and the mixture was stirred for 5 min. The mixture was extracted with ether, and the combined extracts were extracted with 1N KOH (10 mL). The aqueous extracts were filtered and acidified to pH 3 with 2N HCl. The precipitate was collected by filtration to give 306 mg (48%) of product as an off-white solid, mp 112°-115° C.

後処理

  1. additionwas added
  2. temperaturethe mixture was warmed slightly with a heat gun
  3. stirringthe mixture was stirred for 5 min
  4. extractionThe mixture was extracted with ether
  5. extractionthe combined extracts were extracted with 1N KOH (10 mL)
  6. filtrationThe aqueous extracts were filtered
  7. filtrationThe precipitate was collected by filtration

出典と根拠

ORDレコード
ord-9f6d11ca37e94e23a068d368b7e5b3cc
出典データセット
uspto-grants-1996_03
特許番号
US05498776

反応ノート

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