Pentabromophenol → Pentabromophenyl 2-(chloromethyl)benzoate

HRID 2419172Notes

Reaction equation

HRID 2419172 reaction equation
[OH-].[Na+].[Br:3][C:4]1[C:9]([OH:10])=[C:8]([Br:11])[C:7]([Br:12])=[C:6]([Br:13])[C:5]=1[Br:14].C1([O-])C=CC=CC=1.[Cl:22][CH2:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>COCCO>[Br:3][C:4]1[C:9]([O:10][C:26](=[O:27])[C:25]2[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=2[CH2:23][Cl:22])=[C:8]([Br:11])[C:7]([Br:12])=[C:6]([Br:13])[C:5]=1[Br:14]

Participants

6

Reactant 4

HCID 11852PentabromophenolHCID 14798Sodium HydroxideHCID 119047PhenolateHCID 30163952-(Chloromethyl)benzoyl chloride

Product 1

HCID 20314961Pentabromophenyl 2-(chloromethyl)benzoateYield 90.5%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

In a 500-ml three-necked flask, 4 g (= 0.1 mole) of sodium hydroxide was dissolved at 60° C in 270 ml of methyl glycol, and 48.9 g of pentabromophenol was stirred in for the preparation of a phenolate solution, as in Example 8c. At 30° to 34° C, 18.9 g (- 0.1 mole) of o-chloromethylbenzoyl chloride was added drop by drop, with stirring, over a period of about 40 minutes, whereupon a white, crystalline preciptate settled out, which after 1 hour was suction filtered. After the product had been stirred up in water, suction filtered, washed and dried, 58 g (= 90.5%) of o-chloromethylbenzoic acid pentabromophenyl ester was obtained, which melted at 201°-205° C.

Workup

  1. waitwhich after 1 hour was
  2. filtrationsuction filtered
  3. stirringAfter the product had been stirred up in water
  4. filtrationsuction filtered
  5. washwashed
  6. customdried

Sources & evidence

ORD record
ord-5a0a2c85d7d44f8b8138fa555004636b
Source dataset
uspto-grants-1978_08
Patent number
US04105628

Reaction notes

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