Triethylamine → 5-Bromo-1,2,3-trimethoxybenzene

HRID 48081

Reaction equation

HRID 48081 reaction equation
[P:1]([O-:18])([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([Br:38])[CH:31]=[C:32]([O:36][CH3:37])[C:33]=1[O:34][CH3:35]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH3:26][O:27][C:28]1[CH:29]=[C:30]([Br:38])[CH:31]=[C:32]([O:36][CH3:37])[C:33]=1[O:34][CH3:35].[CH3:37][O:36][C:32]1[CH:31]=[C:30]([P:1](=[O:18])([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[O:2][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:29]=[C:28]([O:27][CH3:26])[C:33]=1[O:34][CH3:35]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 758855-Bromo-1,2,3-trimethoxybenzeneHCID 21904359Dibenzylphosphite

Product 2

HCID 758855-Bromo-1,2,3-trimethoxybenzeneHCID 54545930Dibenzyl 3,4,5-trimethoxyphenylphosphonate

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

3,4,5-Trimethoxybromobenzene is prepared following the procedure of Tetrahedron Lett. 26 (1985):5939-5942. Dibenzyl phosphite is heated in the presence of tetrakis(triphenylphosphine)palladium (0), triethylamine and toluene with 3,4,5-trimethoxybromobenzene to give Dibenzyl 3,4,5-trimethoxyphenylphosphonate 2 following the procedure of J. Med. Chem. 32 (1989):1580-1590.

Sources & evidence

ORD record
ord-8730786c37d3449cb6fbbde0de98428f
Source dataset
uspto-grants-2004_03
Patent number
US06702705B1

Linked notes

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