Trimethyl borate → 4-(1,3-Dioxolan-2-yl)-3-(trifluoromethyl)phenylboronic acid

HRID 70324

반응식

HRID 70324 반응식
I[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.C([Mg]Cl)(C)C.[B:22](OC)([O:25]C)[O:23]C.C(OB1OC(C)(C)C(C)(C)O1)(C)C>>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:5]1[CH:6]=[CH:7][C:2]([B:22]([OH:25])[OH:23])=[CH:3][C:4]=1[C:13]([F:16])([F:15])[F:14]

참가 물질

5

반응물 4

HCID 8470Trimethyl borateHCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 582766812-[4-Iodo-2-(trifluoromethyl)phenyl]-1,3-dioxolaneHCID 178418918HCID 178418918, 화합물

생성물 1

HCID 582764504-(1,3-Dioxolan-2-yl)-3-(trifluoromethyl)phenylboronic acid

실험 절차

The title compound was prepared from 2-[4-iodo-2-(trifluoromethyl)phenyl]-1,3-dioxolane (Example I-IX-7) according to the procedure described for Example V-18, with the following exceptions: the aryl iodide and i-PrMgCl were aged 45 min before introduction of the electrophile (instead of 30 min); trimethyl borate was used as the electrophile (instead of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane); the dried organic extracts were concentrated to dryness and triturated with Et2O/hexanes (instead of flash chromatography). White solid. LC/MS (method A) 2.22 min, m/z 417 ({2[M-gylcol]-H2O}—H, 23%), 217 ([M-glycol]-H, 57%), 189 (100%, −ve ion).

후처리

  1. concentrationthe dried organic extracts were concentrated to dryness
  2. customtriturated with Et2O/hexanes (instead of flash chromatography)
  3. customLC/MS (method A) 2.22 min, m/z 417 ({2[M-gylcol]-H2O}—H, 23%), 217 ([M-glycol]-H, 57%), 189 (100%, −ve ion)

출처 및 근거

ORD 기록
ord-d0034df33c7d499db45ff337c85d8550
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822518B2

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