Carbon tetrabromide → HCID 67357394, compound

HRID 1407443Notes

Reaction equation

HRID 1407443 reaction equation
[F:1][C:2]1[C:10]2[O:9][C:8]([CH2:11]O)=[CH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Br:13]C(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:13][CH2:11][C:8]1[O:9][C:10]2[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 65426139HCID 65426139, compound

Product 1

HCID 67357394HCID 67357394, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (7-fluorobenzofuran-2-yl)methanol (1.38 g, 8.31 mmol), tetrabromomethane (4.41 g, 13.3 mmol) and triphenylphosphine (2.61 g, 9.97 mmol) in dichloromethane (42 mL) was stirred at 0° C. for 2 h and concentrated in vacuo to dryness. The residue was purified by column chromatography (hexanes/ethyl acetate, 49/1) to afford 2-(bromomethyl)-7-fluorobenzofuran (1.85 g, 97%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ7.34-7.29 (m, 1H), 7.20-7.12 (m, 1H), 7.10-7.02 (m, 1H), 6.82-6.77 (m, 1H), 4.60 (s, 2H).

Workup

  1. concentrationconcentrated in vacuo to dryness
  2. customThe residue was purified by column chromatography (hexanes/ethyl acetate, 49/1)

Sources & evidence

ORD record
ord-96386a1386054c1c86e71a642ca3a587
Source dataset
uspto-grants-2014_12
Patent number
US08916580B2

Reaction notes

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