Hexane → (2-Bromomethylbenzyloxy)-t-butyldiphenylsilane

HRID 748815Notes

Reaction equation

HRID 748815 reaction equation
[Si:1]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH2:26]O)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Br)(Br)(Br)[Br:29].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCCCCC>ClCCl.C(OCC)(=O)C>[Br:29][CH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8058HexaneHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 11440297[2-[(t-Butyldiphenylsilyloxy)methyl]phenyl]methanol

Product 1

HCID 59750893(2-Bromomethylbenzyloxy)-t-butyldiphenylsilaneYield 89.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In dichloromethane (50 ml) were dissolved [2-[(t-butyldiphenylsilyloxy)methyl]phenyl]methanol (3.00 g, 7.97 mmol) and carbon tetrabromide (3.40 g, 10.3 mmol). Under ice cooling, a dichloromethane solution (5 ml) of triphenylphosphine (2.70 g, 10.3 mmol) was added dropwise. After stirring at room temperature for 14 hours, the reaction mixture was concentrated under reduced pressure. The residue thus obtained was subjected to silica gel chromatography. The fraction obtained from the hexane:ethyl acetate=30:1 eluate was concentrated under reduced pressure, whereby the title compound (3.12 g, 7.10 mmol, 89%) was obtained as a colorless oil.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue thus obtained

Sources & evidence

ORD record
ord-a4d8991de3e0447aaa3b2ac3885fc3c5
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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