N-bromobutanimide → HCID 12703975, compound

HRID 1902887Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([CH3:14])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O>>[Br:15][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11]([CH3:14])=[CH:12][N:13]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 67184N-bromobutanimide

HCID 12703695HCID 12703695, compound

Product 1

HCID 12703975HCID 12703975, compound

Procedure

Reaction of the above 2-(4-methylphenyl)-5-methylpyrimidine with N-bromosuccinimide, as described in Example 15, affords 2-(4-bromomethylphenyl)-5-methylpyrimidine with a melting point of 129°-131° C. (recrystallisation from ligroin). With stirring, a mixture of 184 g of 2-(4-bromomethylphenyl)-5-methylpyrimidine and 465 g of triethylphosphite is slowly heated to 150° C., while simultaneously distilling off ethyl bromide, and then stirred for 5 hours at this temperature. Excess triethylphosphite is distilled off, affording 220 g of the phosphonate in the form of a light brown viscous oil.

Sources & evidence

ORD record: ord-20d5360304c947f9a1686b2ce3153512
Source dataset: uspto-grants-1982_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04366189

Reaction notes

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