A painting by renowned portrait artist Lucian Freud is expected to break the artist's record when it goes on sale at Christie's auction house in London.
Freud painted the portrait in 1992
The portrait of Freud's close friend and picture editor Bruce Bernard, painted in 1992, is expected to fetch between £4.5m and £5.5m.
The post-war and contemporary art evening sale takes place on 20 June.
The current record for a Freud work was set by Red-Haired Man in a Chair, which sold for £4.1m at Christie's in 2005.
Other paintings on offer include Francis Bacon's Two Men Working in a Field (1971), which is estimated to sell for between £5m and £7m.
Frank Auerbach's Time in Mornington Crescent is also up for sale, alongside works by Paula Rego, Michael Andrews, Leon Kossof and RB Kitaj.
All the works on sale are from a private collection owned by Elaine and Melvin Merians, who began to collect paintings from a group known as the School of London artists in 1978.
Pilar Ordovas, head of post-war and contemporary art at Christie's, described the Bernard portrait as "incredibly powerful".
Bernard, who died in 2000, was picture editor of the Sunday Times magazine.
He wrote a number of books on photography and painting including a treatise on Freud's work.