Methanol → (R)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol

HRID 1696824Notes

Reaction equation

HRID 1696824 reaction equation
B.C1COCC1.[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=[O:24])[CH2:22][Br:23])=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CO>C1(C)C=CC=CC=1.C1COCC1>[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C@@H:21]([OH:24])[CH2:22][Br:23])=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 110894102-Bromo-1-(3-nitro-4-phenylmethoxyphenyl)ethanone

Product 1

HCID 10882679(R)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of BH3.THF in THF (1 M, 3.70 mL, 3.70 mmol) was added to a solution of 1-(4-benzyloxy-3-nitrophenyl)-2-bromoethanone (3) (1.08 g, 3.08 mmol) and R-methyl-CBS-oxazoborolidine (1 M in toluene, 0.61 mL, 0.61 mmol) in anhydrous THF (15 mL). The resulting reaction mixture was stirred at rt for 16 h. Methanol (5 mL) was slowly added to quench the reaction. After removal of solvent by rotary evaporation, the resulting residue was purified by Biotage silica gel column chromatography eluting with dichloromethane to give the desired bromo alcohol 4 as a yellow, viscous oil (0.72 g, 66%): 1H NMR (500 MHz, CDCl3) δ 2.82 (d, 1H), 3.48 (dd, 1H), 3.59 (dd, 1H), 4.89 (m, 1H), 5.21 (s, 2H), (d, 1H), 7.39 (m, 5H), 7.50 (dd, 1H), 7.87 (d, 1H).

Workup

  1. customThe resulting reaction mixture
  2. customto quench
  3. customthe reaction
  4. customAfter removal of solvent
  5. customby rotary evaporation
  6. customthe resulting residue was purified by Biotage silica gel column chromatography
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-1f5f0bd8647f41bcbac1df3c2f4b4dcf
Source dataset
uspto-grants-2012_04
Patent number
US08163758B2

Reaction notes

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