Trimethyl phosphite → HCID 21805256, compound

HRID 1938816Notes

Reaction equation

HRID 1938816 reaction equation
[P:1]([O:6][CH3:7])([O:4][CH3:5])[O:2]C.[Br:8][C:9]1[C:10]([OH:19])=[C:11]([CH:14]=[C:15]([O:17][CH3:18])[CH:16]=1)[CH2:12]Br>>[CH3:5][O:4][P:1]([CH2:12][C:11]1[CH:14]=[C:15]([O:17][CH3:18])[CH:16]=[C:9]([Br:8])[C:10]=1[OH:19])(=[O:2])[O:6][CH3:7]

Participants

3

Reactant 2

HCID 8472Trimethyl phosphiteHCID 21470007HCID 21470007, compound

Product 1

HCID 21805256HCID 21805256, compound

Procedure

8.8 g of trimethyl phosphite are added to 20.0 g of 3-bromo-2-hydroxy-5-methoxy-benzyl bromide and, with stirring, the mixture is heated for 3 hours at 140° (complete conversion according to TLC). The resulting oil is filtered with toluene/ethyl acetate (4:1) as eluant over a small amount of silica gel. [(3-Bromo-2-hydroxy-5-methoxy-phenyl)methyl ]phosphonic acid dimethyl ester is thus obtained [1H-NMR (360 MHz, CDCl3); 3.20 (d, 2H, CH2P, 2JP-H =21 Hz), 3.70 (s, 3H, OCH3), 3.74 (d, 6H, 2×OCH3,3JP-H =1 Hz), 6.70 (m, 1H), 7.07 (m, 1H) ppm].

Workup

  1. temperaturethe mixture is heated for 3 hours at 140° (complete conversion according to TLC)
  2. filtrationThe resulting oil is filtered with toluene/ethyl acetate (4:1) as eluant over a small amount of silica gel

Sources & evidence

ORD record
ord-c095543eb53040e7aea115c8400a08d4
Source dataset
uspto-grants-1997_12
Patent number
US05693807

Reaction notes

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