Water → 3-(4-Bromophenyl)propane-1,2-diol

HRID 2261432Notes

Reaction equation

HRID 2261432 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][CH:5]=1)C=C.C[N+]1([O-])[CH2:17][CH2:16][O:15]CC1.[OH2:19]>CC(C)=O.C(Cl)Cl.O=[Os](=O)(=O)=O>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([CH2:1][CH:16]([OH:15])[CH2:17][OH:19])=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 137529Benzene, 1-bromo-4-(2-propenyl)-

Product 1

HCID 203327403-(4-Bromophenyl)propane-1,2-diol

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-allyl-4-bromo-benzene (2.0 g, 10.2 mmol) in acetone (60 mL) is treated with OsO4 (52 mg, 0.20 mmol), NMO (1.44 g, 12.2 mmol) and water (approx. 0.3 mL). The clear solution is stirred at rt for 2 h, diluted with DCM (150 mL) and washed twice with 10% aq. citric acid (2×75 mL). The aqueous phase is extracted twice with DCM. The organic extracts are combined, dried over MgSO4 and evaporated. The crude product is purified by CC on silica gel eluting with EA to give 3-(4-bromo-phenyl)-propane-1,2-diol (1.41 g) as an almost colourless oil; LC-MS: tR=0.72 min; 1H NMR (CDCl3): δ 7.46-7.40 (m, 2H), 7.14-7.08 (m, 2H), 3.96-3.87 (m, 1H), 3.73-3.67 (m, 1H), 3.55-3.47 (m, 1H), 2.81-2.67 (m, 2H), 1.90 (s br, 2H).

Workup

  1. washwashed twice with 10% aq. citric acid (2×75 mL)
  2. extractionThe aqueous phase is extracted twice with DCM
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe crude product is purified by CC on silica gel eluting with EA

Sources & evidence

ORD record
ord-c57af3846a0d42c986fffa12a24cd2ab
Source dataset
uspto-grants-2010_12
Patent number
US07846964B2

Reaction notes

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