5-Bromo-2-hydroxybenzophenone → 4-Bromo-2-(hydroxy-phenyl-methyl)-phenol

HRID 971336

반응식

HRID 971336 반응식
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([OH:18])=[C:8]([C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:11])[CH:9]=1>CO>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([OH:18])=[C:8]([CH:10]([OH:11])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=1

참가 물질

4

반응물 2

HCID 2290095-Bromo-2-hydroxybenzophenoneHCID 4311764Sodium borohydride

생성물 1

HCID 121347074-Bromo-2-(hydroxy-phenyl-methyl)-phenol수율 98%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

1.02 g (27 mmol, 3.9 eqv) NaBH4 was added cautiously at rt to a solution of 1.92 g (6.9 mmol) (5-Bromo-2-hydroxy-phenyl)-phenyl-methanone (18) in 70 ml dry MeOH. After stirring this solution for 2 h at rt the solvent was evaporated and the residue was taken up in 70 ml water and 70 ml Et2O. The aq. layer was extracted with Et2O and the comb. org. fractions were washed twice with water, dried over Na2SO4 and evaporated. Column chromatography (Hexanes/EtOAc (1+1)) yielded 1.88 g (6.7 mmol, 98%) 19 as a white solid: Rf (Hexanes/EtOAc (1+1)) 0.57; mp 96-97° C.; 1H NMR (500 MHz, CDCl3) δ 2.76 (d, 1H, J=3.15 Hz), 5.98 (d, 1H, J=3.00 Hz), 6.79 (d, 1H, J=8.67 Hz), 6.98 (dd, 1H, J1=2.21 Hz, J2=0.47 Hz), 7.28 (dd, 1H, J1=8.67 Hz, J2=2.36 Hz), 7.33-7.41 (m, 5H), 7.92 (s, 1H); LRMS (EI) m/z 278 (5), 276 (4), 262 (56), 261 (100), 260 (46), 259 (95), 181 (21), 180 (12), 153 (12), 152 (33), 77 (16), 76 (16), 63 (10); HRMS (EI) Calcd. for C13H11BrO2: 277.994241. Found: 277.993366.

후처리

  1. customwas evaporated
  2. extractionThe aq. layer was extracted with Et2O
  3. washfractions were washed twice with water
  4. dry with materialdried over Na2SO4
  5. customevaporated

출처 및 근거

ORD 기록
ord-f512156f95fd43959e4abe1745c5dc61
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07312246B2

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