p-Bromobenzhydryl alcohol → HCID 59232670, compound

HRID 2426981Notes

Reaction equation

HRID 2426981 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)O)=[CH:4][CH:3]=1.[CH3:16][O:17][C:18]([O:22][Si](C)(C)C)=[C:19]([CH3:21])[CH3:20]>[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:19]([CH3:21])([CH3:20])[C:18]([O:17][CH3:16])=[O:22])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 98221p-Bromobenzhydryl alcoholHCID 552336Silane, ((1-methoxy-2-methyl-1-propenyl)oxy)trimethyl-

Product 1

HCID 59232670HCID 59232670, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 24193Titanium TetrachlorideCatalyst

Procedure

In a similar manner to Preparation 14, Step 2, the reaction of (4-bromophenyl)(phenyl)methanol (10 g, 38 mmol), and (1-methoxy-2-methylprop-1-enyloxy)trimethylsilane (23.2 g, 133 mmol) in the presence of titanium tetrachloride (1M in DCM, 42 ml. 41.8 mmol) afforded methyl 3-(4-bromophenyl)-2,2-dimethyl-3-phenylpropanoate (13 g, 99% yield). LC/MS (m/z) 347.05, 349 [(M+1)+]; HPLC Rt: 4.18 min.

Workup

  1. customIn a similar manner to Preparation 14, Step 2

Sources & evidence

ORD record
ord-6b2a41495a2145b594ce65ed448b275f
Source dataset
uspto-grants-2011_06
Patent number
US07968577B2

Reaction notes

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