Benzene → [4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide

HRID 2198789Notes

Reaction equation

HRID 2198789 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6](C[Br:12])=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:4].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH:32]1C=CC=CC=1>>[Br-:12].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH2:32][P+:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[CH:7][CH:6]=1)([O:2][CH3:1])=[O:4]

Participants

4

Reactant 3

HCID 241BenzeneHCID 11776TriphenylphosphineHCID 2734813Methyl 2-(bromomethyl)benzoate

Product 1

HCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide

Procedure

A mixture of 46 g (0.2 mole) of methyl-α-bromotoluate and 105 g (0.4 mole) of triphenyl phosphine in 800 ml of dry benzene was refluxed for two hours. After 15 minutes, the phosphonium bromide started precipitating out from the solution. After cooling the flask to room temperature, the solid was filtered, washed with plenty of petroleum ether and dried. The yield was 98 g m.p. 258°-260° C. The infrared spectrum showed absorption at 1720 cm-1 ##STR10## NMR (CDCl3) showed 3.8 ##STR11## 5.5-5.8 (d, --CH2 -p+, 2), and 7-8 (m,aromatic, 19). The phosphonium bromide was used in the next stop without further purification.

Workup

  1. temperaturewas refluxed for two hours
  2. customthe phosphonium bromide started precipitating out from the solution
  3. filtrationthe solid was filtered
  4. washwashed with plenty of petroleum ether
  5. customdried
  6. customabsorption at 1720 cm-1 ##STR10## NMR (CDCl3)
  7. customThe phosphonium bromide was used in the next stop without further purification

Sources & evidence

ORD record
ord-a90871c7845548949f1ac2c457f9ca83
Source dataset
uspto-grants-1982_11
Patent number
US04359568

Reaction notes

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