Sodium Hydroxide → HCID 66914131, compound

HRID 2104606Notes

Reaction equation

HRID 2104606 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1O)=[CH:9][CH:8]=[CH:7][C:6]=2[C:13]([F:16])([F:15])[F:14].FC(F)(F)[C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:28]=1N=CC=C2O.BrBr.[OH-].[Na+]>C(O)(=O)C>[C:5]1([C:2]2[CH:3]=[N:4][C:5]3[C:10]([C:11]=2[C:28]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[CH:9][CH:8]=[CH:7][C:6]=3[C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 178515289HCID 178515289, compoundHCID 1785164428-(Trifluoromethyl)quinolin-4-ol

Product 1

HCID 66914131HCID 66914131, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Preparation of 3-Bromo-8-(trifluoromethyl)quinolin-4-ol: 8-Trifluoromethyl-quinolin-4-ol (9.12 g, 42.8 mmol) is dissolved in acetic acid (300 mL). Bromine (2.20 mL 42.8 mmol) is dissolved in acetic acid (30 mL) and then added drop wise to the reaction over 20 min. After 0.5 h, the solution is poured into 500 mL of 2N NaOH and stirred. The white precipitate is filtered and dried in vacuo yielding the title compound as a white solid (10.3 g, 83%). mp 297-299° C.; MS (ESI) m/z 292; MS (ESI) m/z 290; HRMS: calcd for C10H5BrNF3O+H, 291.95848; found (ESI_FT, [M+H]1+), 291.95847.

Workup

  1. additionadded drop
  2. customwise to the reaction over 20 min
  3. filtrationThe white precipitate is filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-bf4b429fb8d847f0aae1f5f9958ec6dc
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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