Triphenylphosphine → 1-(((S)-2-(Bromomethyl)-3-methylbutoxy)methyl)benzene

HRID 660379Notes

Reaction equation

HRID 660379 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]([CH:13]([CH3:15])[CH3:14])[CH2:11]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Br:42])C(=O)C1>C(Cl)Cl>[Br:42][CH2:11][C@@H:10]([CH:13]([CH3:15])[CH3:14])[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 68782329(R)-2-(benzyloxymethyl)-3-methylbutan-1-ol

Product 1

HCID 117159911-(((S)-2-(Bromomethyl)-3-methylbutoxy)methyl)benzeneYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-(benzyloxymethyl)-3-methylbutan-1-ol (54 g, 0.26 mol) in dry CH2Cl2 (2 L) at 0° C., Ph3P (88 g, 0.31 mol) and NBS (55.5 g, 0.31 mol) were added in portions. After stirring for 18 h at rt, the mixture was evaporated and the residue was purified by flash chromatography on silica gel to give (S)-((2-(bromomethyl)-3-methylbutoxy)methyl)benzene (43 g, 61%). 1H NMR (400 MHz, CDCl3): 0.94 (m, 6H), 1.71 (m, 1H), 1.85 (m, 1H), 3.48 (m, 1H), 3.57 (m, 1H), 3.62 (m, 1H), 3.68 (m, 1H), 4.52 (s, 2H), 7.31 (m, 5H)

Workup

  1. customthe mixture was evaporated
  2. customthe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-f352adcaae3645eaaf3220bde80f4d9c
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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