Carbon tetrabromide → 2-(4-Fluoro-benzyl)-benzofuran-5-carbaldehyde

HRID 1171224Notes

Reaction equation

HRID 1171224 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)=[CH:11][C:10]=2[CH:22]=1.C(Br)(Br)(Br)Br.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[F:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][C:12]2[O:13][C:9]3[CH:8]=[CH:7][C:6]([CH:2]=[O:1])=[CH:22][C:10]=3[CH:11]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 68718678HCID 68718678, compound

Product 1

HCID 576082542-(4-Fluoro-benzyl)-benzofuran-5-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a methylene chloride (4 mL) solution of 5-[1,3]dioxolan-2-yl-2-(4-fluoro-benzyl)-benzofuran (100 mg, 0.335 mmol) and carbon tetrabromide (222 mg, 0.67 mmol) was dropped a methylene chloride (1 mL) solution of triphenylphosphine (176 mg, 0.67 mmol), while cooling with ice.

Workup

  1. temperaturewhile cooling with ice

Sources & evidence

ORD record
ord-733b73e6e0bf423a9764411af17f67c7
Source dataset
uspto-grants-2010_11
Patent number
US07829585B2

Reaction notes

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