Carbon tetrabromide → 5-(Bromomethyl)-6-iodoindane

HRID 604614Notes

Reaction equation

HRID 604614 reaction equation
[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH2:8]2)=[CH:4][C:3]=1[CH2:11]O.C(Br)(Br)(Br)[Br:14].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:14][CH2:11][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[I:1])[CH2:8][CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 11205Carbon tetrabromide2×HCID 11776Triphenylphosphine2×HCID 57576294(6-iodo-2,3-dihydro-1H-inden-5-yl)methanol

Product 1

HCID 575443555-(Bromomethyl)-6-iodoindane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-iodo-2,3-dihydro-1H-inden-5-yl)methanol (36 mg, 0.131 mmol) and carbon tetrabromide (52 mg, 0.158 mmol) in CH2Cl2 (1 mL) at 0° C. under N2, was added triphenylphosphine (41 mg, 0.158 mmol). The resulting solution was allowed to warm to room temperature and was stirred for 4 h. Another portion of carbon tetrabromide (52 mg, 0.158 mmol) and triphenylphosphine (41 mg, 0.158 mmol) was added to the mixture at 0° C. The reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo. The residue was purified by flash chromatography (Si, 1% EtOAc in hexanes) to afford 5-(bromomethyl)-6-iodoindane. 1H NMR (500 MHz, CDCl3) δ 7.72 (s, 1H), 7.36 (s, 1H), 4.62 (s, 2H), 2.89 (m, 4H), 2.11-2.07 (m, 2H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by flash chromatography (Si, 1% EtOAc in hexanes)

Sources & evidence

ORD record
ord-aa01116282a241abb930963603823a5c
Source dataset
uspto-grants-2011_03
Patent number
US07910592B2

Reaction notes

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