Carbon tetrabromide → 4-Allyldimethylsilylbenzyl bromide
Reaction equation
[CH2:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8](O)[SiH:9]([CH3:11])[CH3:10])=[CH:6][CH:5]=1)[CH:2]=[CH2:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>>[CH2:1]([C:4]1[CH:14]=[CH:13][C:7]([CH:8]([Br:35])[SiH:9]([CH3:11])[CH3:10])=[CH:6][CH:5]=1)[CH:2]=[CH2:3]Participants
4
Procedure
Reaction of 4-allyldimethylsilylbenzyl alcohol (3 Scheme 1) with triphenylphosphine and carbon tetrabromide gave 4-allyldimethylsilylbenzyl bromide (4 Scheme 13). Subsequent reaction with potassium cyanide gave 4-allyldimethylsilylphenylacetonitrile (6 Scheme 13). Under the usual coupling conditions, this was loaded to the polymer and the loading level of resin (2 Scheme 13, 0.23 mequiv/g) was determined by the mass balance of 4-bromophenylacetonitrile which was obtained from cleavage reaction of the resin with bromine.
Sources & evidence
- ORD record
- ord-8d93bd4cbe604a6d82dd9b66b3a9a8e7
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06416861B1
Reaction notes
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