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

HRID 971336

反応式

HRID 971336 の反応式
[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

参加物

4

反応物 2

HCID 2290095-Bromo-2-hydroxybenzophenoneHCID 4311764Sodium borohydride

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f512156f95fd43959e4abe1745c5dc61
出典データセット
uspto-grants-2007_12
特許番号
US07312246B2

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