Hydrogen Bromide → Bis(2-chlorophenyl)-bromomethane

HRID 2373534Notes

Reaction equation

HRID 2373534 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:16])O.[BrH:17].O>C(O)(=O)C>[Br:17][CH:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[Cl:16])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 962WaterHCID 230561Bis(2-chlorophenyl)methanol

Product 1

HCID 826777Bis(2-chlorophenyl)-bromomethane

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
22.5 °C

Procedure

Under N2, bis(2-chlorophenyl)methanol (70 g, 0.28 mol) was added in 4 portions at 20 to 25° C. to HBr (97 ml) in acetic acid (33% by weight). The mixture was stirred at 20 to 25° C. and the reaction was followed by HPLC. After complete reaction (60 to 90 min), the mixture was cooled to 0 to 10° C. and water (700 ml) was added over 30 min. The suspension was stirred at 0 to 10° C. for a further 30 min. The product was isolated by filtration and washed with water (4×140 ml). The product was dried under vacuum at 25° C. to constant weight. Yield: 82.6 g (95%). Assay (HPLC): 100% pure vs. standard

Workup

  1. customAfter complete reaction (60 to 90 min)
  2. temperaturethe mixture was cooled to 0 to 10° C.
  3. stirringThe suspension was stirred at 0 to 10° C. for a further 30 min
  4. customThe product was isolated by filtration
  5. washwashed with water (4×140 ml)
  6. customThe product was dried under vacuum at 25° C. to constant weight

Sources & evidence

ORD record
ord-f00c64155e264cb4a7fd3e8a2d6d9007
Source dataset
uspto-grants-2008_12
Patent number
US07459556B2

Reaction notes

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