Bromoacetyl bromide → HCID 12517307, compound

HRID 2083007Notes

Reaction equation

HRID 2083007 reaction equation
[NH2:1][C:2]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])=[CH:8][CH:7]=1)=[O:5].[Br:24][CH2:25][C:26](Br)=[O:27].C(=O)(O)[O-].[Na+]>CCOCC>[Br:24][CH2:25][C:26]([NH:1][C:2]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:3]=1[C:4]([C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:18])[C:14]([F:15])([F:16])[F:17])=[CH:10][CH:11]=1)=[O:5])=[O:27]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 516892Sodium BicarbonateHCID 12517303HCID 12517303, compound

Product 1

HCID 12517307HCID 12517307, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred mixture of 56 g (0.163 mole) of 2-amino-5-chloro-4'-(2,2,2-trifluoroacetamido)-benzophenone in 900 ml of ether was added 43 g (0.213 mole) of bromoacetyl bromide and a saturated aqueous solution of sodium bicarbonate in portions, keeping the solution slightly basis during the addition. The reaction was stirred for 90 min and filtered to give 66 g of product. The ether layer was dried and evaporated and the residual oil was crystallized from methanol to give an additional 10 g of the product for a total yield of 76 g (96%). Recrystallization from a mixture of dichloromethane, methanol and petroleum ether gave an analytical sample of off white rods, mp 198°-201° ir (KBr) 1750, 1663, 1640 cm-1 (3C=O).

Workup

  1. additionduring the addition
  2. filtrationfiltered

Sources & evidence

ORD record
ord-cf1fcc11b0234f4eabd2aa8cfe3019ef
Source dataset
uspto-grants-1978_04
Patent number
US04083948

Reaction notes

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