Carbon tetrabromide → 2-(6-Bromohexylthio)acetaldehyde

HRID 471231Notes

Reaction equation

HRID 471231 reaction equation
C[O:2][CH:3](OC)[CH2:4][S:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]O.C(Br)(Br)(Br)[Br:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:16][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][S:5][CH2:4][CH:3]=[O:2]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 579890516-(2,2-Dimethoxyethylthio)hexan-1-ol

Product 1

HCID 579889152-(6-Bromohexylthio)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(2,2-dimethoxyethylthio)hexan-1-ol (example 101, step a) (1.85 g) in DCM (75 mL) at 0° C. under N2 was added carbon tetrabromide (3.31 g) followed by triphenylphosphine (2.62 g) portionwise. The resultant mixture was stirred at RT for 1.25 h then concentrated in vacuo. Purification was by silica gel chromatography eluting with 0-50% ethyl acetate in cyclohexane to give the subtitled compound as a yellow liquid. Yield 1.31 g.

Workup

  1. concentrationthen concentrated in vacuo
  2. customPurification
  3. washeluting with 0-50% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-583b52a709b74d64808cfbc1cbc36155
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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