Carbon tetrabromide → HCID 66603538, compound

HRID 1627932Notes

Reaction equation

HRID 1627932 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:3]=1[CH2:22]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:44]>ClCCl>[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)[C:3]=1[CH2:22][Br:44]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 66603499HCID 66603499, compound

Product 1

HCID 66603538HCID 66603538, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2-methyl-4-(p-tolyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl)methanol (0.323 g; 1 mmol) in dry dichloromethane (5 mL) were added triphenylphosphine (0.314 g; 1.2 mmol) and carbon tetrabromide (0.431 g; 1.3 mmol). The resulting solution was stirred for 21 h. The volatiles were removed under reduced pressure and the remaining residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate (1-30%) in heptane to afford 0.310 g (80%) of the title compound as a white solid.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe remaining residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate (1-30%) in heptane

Sources & evidence

ORD record
ord-8b264bba0a6245659f3f68e2d32ec503
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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