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

HRID 971336Notes

Reaction equation

HRID 971336 reaction equation
[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

Participants

4

Reactant 2

HCID 2290095-Bromo-2-hydroxybenzophenoneHCID 4311764Sodium borohydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f512156f95fd43959e4abe1745c5dc61
Source dataset
uspto-grants-2007_12
Patent number
US07312246B2

Reaction notes

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