Carbon tetrabromide → HCID 67358461, compound

HRID 1667200Notes

Reaction equation

HRID 1667200 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[S:5][C:6]=1[CH2:7]O.C(Br)(Br)(Br)[Br:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:20][CH2:7][C:6]1[S:5][C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)=[N:3][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 22647518{4-Methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanol

Product 1

HCID 67358461HCID 67358461, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {4-methyl-2-[3-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanol (90.2 g, 0.732 mmol) in dichloromethane (10 mL) was added carbon tetrabromide (0.485 g, 1.464 mmol) and triphenylphosphine (0.384 g, 1.464 mmol). The reaction mixture was then stirred at room temperature for 16 hours. The reaction mixture was concentrated, and the residue was chromatographed on silica gel eluting with 10-20% ethyl acetate/hexane to yield the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 8.18 (s, 1H), 8.06 (d, J=7.54 Hz, 1H), 7.67 (d, 1H), 7.56 (t, J=7.73 Hz, 1H), 4.72 (m, 2H), 2.48 (m, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was chromatographed on silica gel eluting with 10-20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-734979f180c04c2cad7aff557bb15bbe
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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