Bromine → Thiocyanic acid, 2,3-dihydro-6-(trifluoromethyl)-1H-indol-5-yl ester

HRID 989165Notes

Reaction equation

HRID 989165 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][NH:9]2)=[CH:5][CH:4]=1.[S-:14][C:15]#[N:16].[K+].BrBr>CO>[S:14]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][C:3]=1[C:2]([F:1])([F:12])[F:13])[NH:9][CH2:8][CH2:7]2)[C:15]#[N:16]

Participants

5

Reactant 3

HCID 24408BromineHCID 516872Potassium thiocyanateHCID 101764376-(Trifluoromethyl)indoline

Product 1

HCID 10610283Thiocyanic acid, 2,3-dihydro-6-(trifluoromethyl)-1H-indol-5-yl esterYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of trifluoromethylindoline (D1) (9.7 g, 52 mmol) and potassium thiocyanate (10.09 g, 104 mmol) in methanol (200 ml) was treated with a solution of bromine (2.82 ml, 55 mmol) in methanol (35 ml) dropwise over 0.5 h at −5-0° C. The reaction mixture was allowed to warm to room temperature and stirred overnight then evaporated to dryness. The residue was partitioned between aqueous K2CO3 (100 ml) and dichloromethane (3×100 ml). The combined extracts were dried (Na2SO4) and evaporated and the residue chromatographed on silica using 2-30% ethyl acetate/petroleum ether as eluant to afford the title compound (9.1 g, 72%) as a yellow solid

Workup

  1. customthen evaporated to dryness
  2. customThe residue was partitioned between aqueous K2CO3 (100 ml) and dichloromethane (3×100 ml)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. customevaporated
  5. customthe residue chromatographed on silica using 2-30% ethyl acetate/petroleum ether as eluant

Sources & evidence

ORD record
ord-5442307bae824ea9aae7985800a7252d
Source dataset
uspto-grants-2003_10
Patent number
US06638953B2

Reaction notes

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